CH620205A5 - - Google Patents

Download PDF

Info

Publication number: CH620205A5
Authority: CH; Switzerland
Prior art keywords: chloro; preparation; benzophenone; imidazole; title compound
Prior art date: 1975-03-28

Application number

CH337476A

Other languages

German (de)

English (en)

Inventor

Martin Gall

Original Assignee

Upjohn Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-03-28

Filing date

1976-03-17

Publication date

1980-11-14

1976-03-17 Application filed by Upjohn Co filed Critical Upjohn Co

1980-11-14 Publication of CH620205A5 publication Critical patent/CH620205A5/de

Links

238000002360 preparation method Methods 0.000 claims description 115
150000001875 compounds Chemical class 0.000 claims description 102
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 42
239000000460 chlorine Chemical group 0.000 claims description 41
238000000034 method Methods 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
239000012965 benzophenone Substances 0.000 claims description 23
239000011737 fluorine Chemical group 0.000 claims description 22
229910052731 fluorine Inorganic materials 0.000 claims description 22
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 21
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 20
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 20
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
229910052801 chlorine Inorganic materials 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 15
150000002431 hydrogen Chemical group 0.000 claims description 12
229930040373 Paraformaldehyde Natural products 0.000 claims description 11
229920002866 paraformaldehyde Polymers 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
SAXQXOAPEGGWSN-UHFFFAOYSA-N [5-chloro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]-phenylmethanone Chemical compound OCC1=NC=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 SAXQXOAPEGGWSN-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 177
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 60
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
239000000047 product Substances 0.000 description 36
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 31
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 23
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 23
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 23
229940024874 benzophenone Drugs 0.000 description 20
239000003921 oil Substances 0.000 description 19
235000019198 oils Nutrition 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
239000003810 Jones reagent Substances 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 10
QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 10
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
-1 alkyl radical Chemical class 0.000 description 9
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 9
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 9
239000008098 formaldehyde solution Substances 0.000 description 9
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 9
239000008096 xylene Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
VLRWWADMWHAHFZ-UHFFFAOYSA-N 2-benzyl-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1CC1=CC=CC=C1 VLRWWADMWHAHFZ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000000538 analytical sample Substances 0.000 description 4
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
239000000155 melt Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
URKLWYBPBQWGTG-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-(2-chlorophenyl)methanone Chemical compound C=1C(Cl)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1Cl URKLWYBPBQWGTG-UHFFFAOYSA-N 0.000 description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
WPRRWTZCKYTGRJ-UHFFFAOYSA-N 4-chloro-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C(Cl)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 WPRRWTZCKYTGRJ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
YKKLPDOLJVNCBF-UHFFFAOYSA-N (2-chlorophenyl)-(2-imidazol-1-yl-5-nitrophenyl)methanone Chemical compound C=1C([N+](=O)[O-])=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1Cl YKKLPDOLJVNCBF-UHFFFAOYSA-N 0.000 description 2
ZFUFQUSCTWEWFI-UHFFFAOYSA-N (2-chlorophenyl)-(5-fluoro-2-imidazol-1-ylphenyl)methanone Chemical compound C=1C(F)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1Cl ZFUFQUSCTWEWFI-UHFFFAOYSA-N 0.000 description 2
WOOJTMHSUDJUJL-UHFFFAOYSA-N (2-chlorophenyl)-[2-(5-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]methanone Chemical compound CC1=CN=CN1C1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1Cl WOOJTMHSUDJUJL-UHFFFAOYSA-N 0.000 description 2
JKRMSXLLMZSUGG-UHFFFAOYSA-N (2-chlorophenyl)-[2-(5-methylimidazol-1-yl)-5-nitrophenyl]methanone Chemical compound CC1=CN=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl JKRMSXLLMZSUGG-UHFFFAOYSA-N 0.000 description 2
MWFJJVCTYISQLC-UHFFFAOYSA-N (2-chlorophenyl)-[2-[2-(hydroxymethyl)-5-methylimidazol-1-yl]-5-nitrophenyl]methanone Chemical compound CC1=CN=C(CO)N1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl MWFJJVCTYISQLC-UHFFFAOYSA-N 0.000 description 2
BXZNCJBWROPOIP-UHFFFAOYSA-N (2-imidazol-1-ylphenyl)-phenylmethanone Chemical class C=1C=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 BXZNCJBWROPOIP-UHFFFAOYSA-N 0.000 description 2
HVSGXVNTRJXGBF-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC(Cl)=CC=C1N1C=NC=C1 HVSGXVNTRJXGBF-UHFFFAOYSA-N 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
CWLUWEMZOXJTET-UHFFFAOYSA-N 2-(c-phenylcarbonohydrazonoyl)-4-(trifluoromethyl)aniline Chemical compound C=1C(C(F)(F)F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 CWLUWEMZOXJTET-UHFFFAOYSA-N 0.000 description 2
LLPGEPRZHOMDHC-SSZFMOIBSA-N 2-[(z)-c-phenylcarbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(N)C=1C(=N/N)\C1=CC=CC=C1 LLPGEPRZHOMDHC-SSZFMOIBSA-N 0.000 description 2
CAALCJWLWAPCKK-UHFFFAOYSA-N 2-[[1-(2-benzoyl-4-chlorophenyl)imidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound C=1C(Cl)=CC=C(N2C(=NC=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 CAALCJWLWAPCKK-UHFFFAOYSA-N 0.000 description 2
UYHUMDTXZYZFSO-UHFFFAOYSA-N 2-[c-(2-chlorophenyl)carbonohydrazonoyl]-4-nitroaniline Chemical compound C=1C([N+]([O-])=O)=CC=C(N)C=1C(=NN)C1=CC=CC=C1Cl UYHUMDTXZYZFSO-UHFFFAOYSA-N 0.000 description 2
VQFDEFHCQYNKMP-UHFFFAOYSA-N 2-[c-(2-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(Cl)C=1C(=NN)C1=CC=CC=C1N VQFDEFHCQYNKMP-UHFFFAOYSA-N 0.000 description 2
NLYWPPDPZODCIP-UHFFFAOYSA-N 4-chloro-2-[(2-chlorophenyl)methyl]aniline Chemical compound NC1=CC=C(Cl)C=C1CC1=CC=CC=C1Cl NLYWPPDPZODCIP-UHFFFAOYSA-N 0.000 description 2
STVQQHQEABMMKA-UHFFFAOYSA-N 4-chloro-2-[c-(2,6-difluorophenyl)carbonohydrazonoyl]aniline Chemical compound FC=1C=CC=C(F)C=1C(=NN)C1=CC(Cl)=CC=C1N STVQQHQEABMMKA-UHFFFAOYSA-N 0.000 description 2
PWQAIHNPIZFUPY-UHFFFAOYSA-N 4-chloro-2-[c-(2-fluorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C(Cl)=CC=C(N)C=1C(=NN)C1=CC=CC=C1F PWQAIHNPIZFUPY-UHFFFAOYSA-N 0.000 description 2
AQKILPKBICMNAC-UHFFFAOYSA-N 4-fluoro-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C(F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 AQKILPKBICMNAC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
PGGRAVWPJMZBEU-UHFFFAOYSA-N [2-(5-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound CC1=CN=CN1C1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 PGGRAVWPJMZBEU-UHFFFAOYSA-N 0.000 description 2
BZEVCGRNCUCATB-UHFFFAOYSA-N [2-imidazol-1-yl-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound C=1C(C(F)(F)F)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 BZEVCGRNCUCATB-UHFFFAOYSA-N 0.000 description 2
WLFCOPOECNTCBJ-UHFFFAOYSA-N [5-bromo-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]-phenylmethanone Chemical compound OCC1=NC=CN1C1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 WLFCOPOECNTCBJ-UHFFFAOYSA-N 0.000 description 2
QLKVVQKZOSBAGN-UHFFFAOYSA-N [5-chloro-2-(5-methylimidazol-1-yl)phenyl]-(2-chlorophenyl)methanone Chemical compound CC1=CN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl QLKVVQKZOSBAGN-UHFFFAOYSA-N 0.000 description 2
RTFYHPFOFWDGRX-UHFFFAOYSA-N [5-chloro-2-(5-methylimidazol-1-yl)phenyl]-phenylmethanone Chemical compound CC1=CN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 RTFYHPFOFWDGRX-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000007857 hydrazones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
DUMGVPIXKALANS-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2,6-difluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=C(F)C=CC=C1F DUMGVPIXKALANS-UHFFFAOYSA-N 0.000 description 1
KWZYIAJRFJVQDO-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl KWZYIAJRFJVQDO-UHFFFAOYSA-N 0.000 description 1
GTGMXPIQRQSORU-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F GTGMXPIQRQSORU-UHFFFAOYSA-N 0.000 description 1
ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
OTBMFWQZXXWHOO-UHFFFAOYSA-N (2-amino-5-fluorophenyl)-phenylmethanone Chemical compound NC1=CC=C(F)C=C1C(=O)C1=CC=CC=C1 OTBMFWQZXXWHOO-UHFFFAOYSA-N 0.000 description 1
GRDGBWVSVMLKBV-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl GRDGBWVSVMLKBV-UHFFFAOYSA-N 0.000 description 1
PZPZDEIASIKHPY-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PZPZDEIASIKHPY-UHFFFAOYSA-N 0.000 description 1
PKSVTEMCGNQIMD-UHFFFAOYSA-N (2-aminophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1Cl PKSVTEMCGNQIMD-UHFFFAOYSA-N 0.000 description 1
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
OILBXOJSIGAQOI-UHFFFAOYSA-N (2-chlorophenyl)-[2-(4,5-dipropylimidazol-1-yl)-5-fluorophenyl]methanone Chemical compound CCCC1=C(CCC)N=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1Cl OILBXOJSIGAQOI-UHFFFAOYSA-N 0.000 description 1
PVMRSLODMXLOPV-UHFFFAOYSA-N (2-chlorophenyl)-[2-(5-ethylimidazol-1-yl)-5-fluorophenyl]methanone Chemical compound CCC1=CN=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1Cl PVMRSLODMXLOPV-UHFFFAOYSA-N 0.000 description 1
YJPYETRZDQKHIT-UHFFFAOYSA-N (2-chlorophenyl)-[2-(5-methylimidazol-1-yl)phenyl]methanone Chemical compound CC1=CN=CN1C1=CC=CC=C1C(=O)C1=CC=CC=C1Cl YJPYETRZDQKHIT-UHFFFAOYSA-N 0.000 description 1
OFORCZVBMNKIKM-UHFFFAOYSA-N (2-chlorophenyl)-[2-[2-(hydroxymethyl)-4,5-dimethylimidazol-1-yl]-5-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)N=C(CO)N1C1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1Cl OFORCZVBMNKIKM-UHFFFAOYSA-N 0.000 description 1
XKGYUGUJRXWPEE-UHFFFAOYSA-N (2-chlorophenyl)-[2-[2-(hydroxymethyl)-5-methylimidazol-1-yl]phenyl]methanone Chemical compound CC1=CN=C(CO)N1C1=CC=CC=C1C(=O)C1=CC=CC=C1Cl XKGYUGUJRXWPEE-UHFFFAOYSA-N 0.000 description 1
QTYYTGOSMSOEIP-UHFFFAOYSA-N (2-chlorophenyl)-[2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]methanone Chemical compound OCC1=NC=CN1C1=CC=CC=C1C(=O)C1=CC=CC=C1Cl QTYYTGOSMSOEIP-UHFFFAOYSA-N 0.000 description 1
HXNQJCCMDFMLFP-UHFFFAOYSA-N (2-chlorophenyl)-[5-fluoro-2-(5-methylimidazol-1-yl)phenyl]methanone Chemical compound CC1=CN=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1Cl HXNQJCCMDFMLFP-UHFFFAOYSA-N 0.000 description 1
LYEMXYGTCWVIRO-UHFFFAOYSA-N (2-chlorophenyl)-[5-fluoro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]methanone Chemical compound OCC1=NC=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1Cl LYEMXYGTCWVIRO-UHFFFAOYSA-N 0.000 description 1
IBSPDPJEJHESCG-UHFFFAOYSA-N (2-imidazol-1-yl-5-nitrophenyl)-phenylmethanone Chemical compound C=1C([N+](=O)[O-])=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 IBSPDPJEJHESCG-UHFFFAOYSA-N 0.000 description 1
SVSOYMDJIIENBL-UHFFFAOYSA-N (3-chlorophenyl)-(2-imidazol-1-ylphenyl)methanone Chemical compound ClC1=CC=CC(C(=O)C=2C(=CC=CC=2)N2C=NC=C2)=C1 SVSOYMDJIIENBL-UHFFFAOYSA-N 0.000 description 1
VHVFCDKTZVYYLO-UHFFFAOYSA-N (4-chloro-2-imidazol-1-ylphenyl)-phenylmethanone Chemical compound C1=CN=CN1C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VHVFCDKTZVYYLO-UHFFFAOYSA-N 0.000 description 1
IITYMENFYXEIBE-UHFFFAOYSA-N (4-chlorophenyl)-[2-[4,5-diethyl-2-(hydroxymethyl)imidazol-1-yl]-3-nitrophenyl]methanone Chemical compound CCC1=C(CC)N=C(CO)N1C1=C(C(=O)C=2C=CC(Cl)=CC=2)C=CC=C1[N+]([O-])=O IITYMENFYXEIBE-UHFFFAOYSA-N 0.000 description 1
TXEOFLUVGBQJHF-UHFFFAOYSA-N (5-bromo-2-imidazol-1-ylphenyl)-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC(Br)=CC=C1N1C=NC=C1 TXEOFLUVGBQJHF-UHFFFAOYSA-N 0.000 description 1
SYMWOLUSGQXJBK-UHFFFAOYSA-N (5-bromo-2-imidazol-1-ylphenyl)-phenylmethanone Chemical compound C=1C(Br)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 SYMWOLUSGQXJBK-UHFFFAOYSA-N 0.000 description 1
GLGWWOSDQYYULY-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-(2,6-difluorophenyl)methanone Chemical compound FC1=CC=CC(F)=C1C(=O)C1=CC(Cl)=CC=C1N1C=NC=C1 GLGWWOSDQYYULY-UHFFFAOYSA-N 0.000 description 1
BSNOZFQHWKCAJO-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC(Cl)=CC=C1N1C=NC=C1 BSNOZFQHWKCAJO-UHFFFAOYSA-N 0.000 description 1
GFEBYYXDXMODAG-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-phenylmethanone Chemical compound C=1C(Cl)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 GFEBYYXDXMODAG-UHFFFAOYSA-N 0.000 description 1
IDCNTSHPGWMKBB-UHFFFAOYSA-N (5-fluoro-2-imidazol-1-ylphenyl)-phenylmethanone Chemical compound C=1C(F)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 IDCNTSHPGWMKBB-UHFFFAOYSA-N 0.000 description 1
SRJCFQCOGAKYLQ-UHFFFAOYSA-N 1-(1,3-dioxolan-2-yl)propan-1-amine Chemical compound CCC(N)C1OCCO1 SRJCFQCOGAKYLQ-UHFFFAOYSA-N 0.000 description 1
UODMKOHXPZDFGW-UHFFFAOYSA-N 2-(C-phenylcarbonohydrazonoyl)-6-(trifluoromethyl)aniline Chemical compound C=1C=CC(C(F)(F)F)=C(N)C=1C(=NN)C1=CC=CC=C1 UODMKOHXPZDFGW-UHFFFAOYSA-N 0.000 description 1
LLPGEPRZHOMDHC-UHFFFAOYSA-N 2-(c-phenylcarbonohydrazonoyl)aniline Chemical class C=1C=CC=C(N)C=1C(=NN)C1=CC=CC=C1 LLPGEPRZHOMDHC-UHFFFAOYSA-N 0.000 description 1
DECLKGWPYCIUIC-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1CC1=CC=CC=C1Cl DECLKGWPYCIUIC-UHFFFAOYSA-N 0.000 description 1
IKJHNXGQANRXPN-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1CC1=CC=CC=C1Cl IKJHNXGQANRXPN-UHFFFAOYSA-N 0.000 description 1
PFFRXFWDKDIUNS-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1Cl PFFRXFWDKDIUNS-UHFFFAOYSA-N 0.000 description 1
OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
OCJHXJOLCAWWIK-UHFFFAOYSA-N 2-[C-(2-chlorophenyl)carbonohydrazonoyl]-4-(trifluoromethyl)aniline Chemical compound C=1C(C(F)(F)F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1Cl OCJHXJOLCAWWIK-UHFFFAOYSA-N 0.000 description 1
GPOHAFSTWZTJPD-UHFFFAOYSA-N 2-[C-(2-chlorophenyl)carbonohydrazonoyl]-4-fluoroaniline Chemical compound C=1C(F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1Cl GPOHAFSTWZTJPD-UHFFFAOYSA-N 0.000 description 1
MVDCSTXXAXPPDO-UHFFFAOYSA-N 2-[C-(2-fluorophenyl)carbonohydrazonoyl]-4-(trifluoromethyl)aniline Chemical compound C=1C(C(F)(F)F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1F MVDCSTXXAXPPDO-UHFFFAOYSA-N 0.000 description 1
NZNYIAUATPUIDV-UHFFFAOYSA-N 2-[C-(3-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(N)C=1C(=NN)C1=CC=CC(Cl)=C1 NZNYIAUATPUIDV-UHFFFAOYSA-N 0.000 description 1
NZSHDXUVEANGRB-UHFFFAOYSA-N 2-[[1-[2-(2-chlorobenzoyl)phenyl]imidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1N1C(CN2C(C3=CC=CC=C3C2=O)=O)=NC=C1 NZSHDXUVEANGRB-UHFFFAOYSA-N 0.000 description 1
IUUUUJSGYMXBBY-UHFFFAOYSA-N 2-[[1-[2-(3-chlorobenzoyl)-3-nitrophenyl]-4-methylimidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=NC(C)=CN1C1=CC=CC([N+]([O-])=O)=C1C(=O)C1=CC=CC(Cl)=C1 IUUUUJSGYMXBBY-UHFFFAOYSA-N 0.000 description 1
LNXOUDXGHIIABD-UHFFFAOYSA-N 2-[[1-[2-benzoyl-4-(trifluoromethyl)phenyl]imidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound C=1C(C(F)(F)F)=CC=C(N2C(=NC=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 LNXOUDXGHIIABD-UHFFFAOYSA-N 0.000 description 1
SRLZVIVUBOKWHU-UHFFFAOYSA-N 2-benzyl-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1CC1=CC=CC=C1 SRLZVIVUBOKWHU-UHFFFAOYSA-N 0.000 description 1
DWOBGCPUQNFAFB-UHFFFAOYSA-N 2-benzylaniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1 DWOBGCPUQNFAFB-UHFFFAOYSA-N 0.000 description 1
UNABNMBJRCOGAD-UHFFFAOYSA-N 2-chloro-6-[C-(2-fluorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C=CC(Cl)=C(N)C=1C(=NN)C1=CC=CC=C1F UNABNMBJRCOGAD-UHFFFAOYSA-N 0.000 description 1
IRDUHPSVEBCHJM-UHFFFAOYSA-N 4-bromo-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C(Br)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 IRDUHPSVEBCHJM-UHFFFAOYSA-N 0.000 description 1
QDNXJINZYNJBDM-UHFFFAOYSA-N 4-bromo-2-[C-(2-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C(Br)=CC=C(N)C=1C(=NN)C1=CC=CC=C1Cl QDNXJINZYNJBDM-UHFFFAOYSA-N 0.000 description 1
QZFAAVBSUXZOIF-UHFFFAOYSA-N 4-bromo-2-[C-(2-fluorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C(Br)=CC=C(N)C=1C(=NN)C1=CC=CC=C1F QZFAAVBSUXZOIF-UHFFFAOYSA-N 0.000 description 1
LKLQROFCQJFPKS-UHFFFAOYSA-N 4-bromo-2-[C-(3-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C(Br)=CC=C(N)C=1C(=NN)C1=CC=CC(Cl)=C1 LKLQROFCQJFPKS-UHFFFAOYSA-N 0.000 description 1
KAGSTLRMFPEMCJ-UHFFFAOYSA-N 4-chloro-2-[(2-fluorophenyl)methyl]aniline Chemical compound NC1=CC=C(Cl)C=C1CC1=CC=CC=C1F KAGSTLRMFPEMCJ-UHFFFAOYSA-N 0.000 description 1
VUFGVUILECQMHD-UHFFFAOYSA-N 4-nitro-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C([N+]([O-])=O)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 VUFGVUILECQMHD-UHFFFAOYSA-N 0.000 description 1
QMHHDXLQEWOUAP-UHFFFAOYSA-N 5-bromo-2-[(2-chlorophenyl)methyl]aniline Chemical compound NC1=CC(Br)=CC=C1CC1=CC=CC=C1Cl QMHHDXLQEWOUAP-UHFFFAOYSA-N 0.000 description 1
SWCGJJRZAVNABK-UHFFFAOYSA-N 5-bromo-2-[C-(2-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(Cl)C=1C(=NN)C1=CC=C(Br)C=C1N SWCGJJRZAVNABK-UHFFFAOYSA-N 0.000 description 1
FRYGXBXYFCYJRR-UHFFFAOYSA-N 5-chloro-2-(C-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C=C(Cl)C=C(N)C=1C(=NN)C1=CC=CC=C1 FRYGXBXYFCYJRR-UHFFFAOYSA-N 0.000 description 1
LRDXYWCCCNFYTO-UHFFFAOYSA-N 5-nitro-2-(C-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C=C([N+]([O-])=O)C=C(N)C=1C(=NN)C1=CC=CC=C1 LRDXYWCCCNFYTO-UHFFFAOYSA-N 0.000 description 1
YSSGEZHDTBOTOL-UHFFFAOYSA-N 6-phenyl-4h-imidazo[1,2-a][1,4]benzodiazepine Chemical compound C12=CC=CC=C2N2C=CN=C2CN=C1C1=CC=CC=C1 YSSGEZHDTBOTOL-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
BSFQEKVYNAAAAG-UHFFFAOYSA-N [2-(4,5-dimethylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound CC1=C(C)N=CN1C1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 BSFQEKVYNAAAAG-UHFFFAOYSA-N 0.000 description 1
LONJJRQATHIDBZ-UHFFFAOYSA-N [2-(5-methylimidazol-1-yl)-5-nitrophenyl]-phenylmethanone Chemical compound CC1=CN=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 LONJJRQATHIDBZ-UHFFFAOYSA-N 0.000 description 1
ITFGTBNIEOFDIE-UHFFFAOYSA-N [2-(5-methylimidazol-1-yl)phenyl]-phenylmethanone Chemical compound CC1=CN=CN1C1=CC=CC=C1C(=O)C1=CC=CC=C1 ITFGTBNIEOFDIE-UHFFFAOYSA-N 0.000 description 1
VIVPMPABXUYDRD-UHFFFAOYSA-N [2-[2-(hydroxymethyl)-5-methylimidazol-1-yl]-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound CC1=CN=C(CO)N1C1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 VIVPMPABXUYDRD-UHFFFAOYSA-N 0.000 description 1
MFSYTJBJBMADDP-UHFFFAOYSA-N [2-[2-(hydroxymethyl)imidazol-1-yl]-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound OCC1=NC=CN1C1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 MFSYTJBJBMADDP-UHFFFAOYSA-N 0.000 description 1
DEYONRMKFVHKOL-UHFFFAOYSA-N [2-[2-(hydroxymethyl)imidazol-1-yl]-5-nitrophenyl]-phenylmethanone Chemical compound OCC1=NC=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 DEYONRMKFVHKOL-UHFFFAOYSA-N 0.000 description 1
NRMOBHGSHDKJLW-UHFFFAOYSA-N [2-amino-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound NC1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 NRMOBHGSHDKJLW-UHFFFAOYSA-N 0.000 description 1
YHESILKRLKYJDT-UHFFFAOYSA-N [2-chloro-6-[2-(hydroxymethyl)-5-methylimidazol-1-yl]phenyl]-phenylmethanone Chemical compound CC1=CN=C(CO)N1C1=CC=CC(Cl)=C1C(=O)C1=CC=CC=C1 YHESILKRLKYJDT-UHFFFAOYSA-N 0.000 description 1
MAOMTOGDSCHWON-UHFFFAOYSA-N [2-imidazol-1-yl-3-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound C1=CN=CN1C=1C(C(F)(F)F)=CC=CC=1C(=O)C1=CC=CC=C1 MAOMTOGDSCHWON-UHFFFAOYSA-N 0.000 description 1
UDDQNFXTQWIKQZ-UHFFFAOYSA-N [3-chloro-2-[2-(hydroxymethyl)-5-methylimidazol-1-yl]phenyl]-phenylmethanone Chemical compound CC1=CN=C(CO)N1C1=C(Cl)C=CC=C1C(=O)C1=CC=CC=C1 UDDQNFXTQWIKQZ-UHFFFAOYSA-N 0.000 description 1
FDTQYDPRCVGILQ-UHFFFAOYSA-N [4-bromo-2-(4,5-diethylimidazol-1-yl)phenyl]-(2-chlorophenyl)methanone Chemical compound CCC1=C(CC)N=CN1C1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1Cl FDTQYDPRCVGILQ-UHFFFAOYSA-N 0.000 description 1
HDRCDPDSMCQICH-UHFFFAOYSA-N [4-chloro-2-(4-methylimidazol-1-yl)phenyl]-(2-chlorophenyl)methanone Chemical compound C1=NC(C)=CN1C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1Cl HDRCDPDSMCQICH-UHFFFAOYSA-N 0.000 description 1
LNGNXXKFSQOJLY-UHFFFAOYSA-N [5-bromo-2-(5-methylimidazol-1-yl)phenyl]-(2-chlorophenyl)methanone Chemical compound CC1=CN=CN1C1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1Cl LNGNXXKFSQOJLY-UHFFFAOYSA-N 0.000 description 1
OECRNCVDVAKJTC-UHFFFAOYSA-N [5-bromo-2-[2-(hydroxymethyl)-5-methylimidazol-1-yl]phenyl]-(2-chlorophenyl)methanone Chemical compound CC1=CN=C(CO)N1C1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1Cl OECRNCVDVAKJTC-UHFFFAOYSA-N 0.000 description 1
PUTMFULCZDJIDG-UHFFFAOYSA-N [5-bromo-2-[4-ethyl-2-(hydroxymethyl)imidazol-1-yl]phenyl]-phenylmethanone Chemical compound OCC1=NC(CC)=CN1C1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 PUTMFULCZDJIDG-UHFFFAOYSA-N 0.000 description 1
JJRVOWRSJFFYJS-UHFFFAOYSA-N [5-chloro-2-(4-methylimidazol-1-yl)phenyl]-(2-chlorophenyl)methanone Chemical compound C1=NC(C)=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl JJRVOWRSJFFYJS-UHFFFAOYSA-N 0.000 description 1
FTNATJWGJDWTID-UHFFFAOYSA-N [5-chloro-2-(5-methylimidazol-1-yl)phenyl]-(2-fluorophenyl)methanone Chemical compound CC1=CN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F FTNATJWGJDWTID-UHFFFAOYSA-N 0.000 description 1
BWUIIPQQUVGUOZ-UHFFFAOYSA-N [5-chloro-2-[2-(hydroxymethyl)-4-methylimidazol-1-yl]phenyl]-(2-chlorophenyl)methanone Chemical compound OCC1=NC(C)=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl BWUIIPQQUVGUOZ-UHFFFAOYSA-N 0.000 description 1
QPBCYQKIJAINAL-UHFFFAOYSA-N [5-chloro-2-[2-(hydroxymethyl)-5-methylimidazol-1-yl]phenyl]-(2-chlorophenyl)methanone Chemical compound CC1=CN=C(CO)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl QPBCYQKIJAINAL-UHFFFAOYSA-N 0.000 description 1
GBAYCXLIRCSEPP-UHFFFAOYSA-N [5-chloro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]-(2,6-difluorophenyl)methanone Chemical compound OCC1=NC=CN1C1=CC=C(Cl)C=C1C(=O)C1=C(F)C=CC=C1F GBAYCXLIRCSEPP-UHFFFAOYSA-N 0.000 description 1
XUQBPNYWNZJNPK-UHFFFAOYSA-N [5-fluoro-2-(5-methylimidazol-1-yl)phenyl]-phenylmethanone Chemical compound CC1=CN=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1 XUQBPNYWNZJNPK-UHFFFAOYSA-N 0.000 description 1
FYKVOVUJLHFZBS-UHFFFAOYSA-N [5-fluoro-2-(5-propan-2-ylimidazol-1-yl)phenyl]-phenylmethanone Chemical compound CC(C)C1=CN=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1 FYKVOVUJLHFZBS-UHFFFAOYSA-N 0.000 description 1
ZLJPKECIQQJHMW-UHFFFAOYSA-N [5-fluoro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]-phenylmethanone Chemical compound OCC1=NC=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1 ZLJPKECIQQJHMW-UHFFFAOYSA-N 0.000 description 1
OKNYYHGNXHEYON-UHFFFAOYSA-N [5-nitro-2-(5-propylimidazol-1-yl)phenyl]-phenylmethanone Chemical compound CCCC1=CN=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 OKNYYHGNXHEYON-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
ZLCSDWSOHXREBD-UHFFFAOYSA-N phenyl-(2-pyrrol-1-ylphenyl)methanone Chemical compound C=1C=CC=C(N2C=CC=C2)C=1C(=O)C1=CC=CC=C1 ZLCSDWSOHXREBD-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH337476A 1975-03-28 1976-03-17 CH620205A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/563,079 US3941803A (en)	1975-03-28	1975-03-28	2-(Imidazol-1-yl)benzophenones

Publications (1)

Publication Number	Publication Date
CH620205A5 true CH620205A5 (fr)	1980-11-14

Family

ID=24249029

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH337476A CH620205A5 (fr)	1975-03-28	1976-03-17

Country Status (5)

Country	Link
US (1)	US3941803A (fr)
JP (1)	JPS51125388A (fr)
CA (1)	CA1059522A (fr)
CH (1)	CH620205A5 (fr)
PL (1)	PL102153B1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4105852A (en) *	1974-08-20	1978-08-08	Hoffmann-La Roche Inc.	Substituted phenyl ketones
US4194049A (en) *	1979-03-29	1980-03-18	Hoffmann-La Roche Inc.	2-[[2-Methyl-1-[2-benzoyl(or benzyl)phenyl]-1H-imidazol-5-yl]methyl]-1H-isoindole-1,3(2H)-diones
EP0275639B1 (fr) *	1986-11-27	1992-07-15	Beecham Group Plc	Amines cycliques N-substituées, leur préparation et compositions pharmaceutiques les contenant
US4912226A (en) *	1987-12-29	1990-03-27	Smithkline Beckman Corporation	Intermediate to dopamine-β-hydroxylase inhibitors
AU2001241084A1 (en) *	2000-03-13	2001-09-24	Taisho Pharmaceutical Co. Ltd.	Imidazolylbenzophenone derivatives
WO2015200766A2 (fr)	2014-06-26	2015-12-30	The Johns Hopkins University	Modulateurs allostériques positifs au gaba restreints au système nerveux périphérique pour le traitement du syndrome du côlon irritable et autres affections du système nerveux périphérique

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3534061A (en) *	1967-12-04	1970-10-13	Parke Davis & Co	N-(alpha-(p-methoxyphenyl)-beta-nitrostyryl)-phenoxyalkyl pyrroles
US3763179A (en) *	1972-05-05	1973-10-02	Upjohn Co	2-imidazol-1-yl benzophenones

1975
- 1975-03-28 US US05/563,079 patent/US3941803A/en not_active Expired - Lifetime
1976
- 1976-01-30 CA CA244,659A patent/CA1059522A/fr not_active Expired
- 1976-03-17 CH CH337476A patent/CH620205A5/de not_active IP Right Cessation
- 1976-03-27 PL PL1976188291A patent/PL102153B1/pl unknown
- 1976-03-29 JP JP51035104A patent/JPS51125388A/ja active Pending

Also Published As

Publication number	Publication date
PL102153B1 (pl)	1979-03-31
US3941803A (en)	1976-03-02
CA1059522A (fr)	1979-07-31
JPS51125388A (en)	1976-11-01

Legal Events

Date	Code	Title	Description
1984-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3337937A1 (de)	1984-05-03	Neue azolderivate
EP0726900A1 (fr)	1996-08-21	7H-IMIDAZO(1,2-a)PYRAZINE-8-ONE ANTAGONISTES DU RECEPTEUR NMDA
CH643736A5 (de)	1984-06-29	Pharmazeutische zubereitungen, enthaltend imidazolderivate oder deren salze.
EP0778271A2 (fr)	1997-06-11	Composés benzo-hétérocycliques à substituant aminoalkyle
EP0112284A2 (fr)	1984-06-27	Dérivés d'éthers arylphényliques
DE2149249A1 (de)	1972-04-13	6-Arylpyrimidine
CH620205A5 (fr)	1980-11-14
CH622019A5 (en)	1981-03-13	Process for the preparation of aminotriazolobenzodiazepines
EP0008804A1 (fr)	1980-03-19	Imidazolylvinyléthers, procédé pour leur préparation, leur utilisation en tant que matières actives dans des produits pharmaceutiques et biocides
WO1999054314A1 (fr)	1999-10-28	Nouveaux heterocycles a 5 noyaux a substitution diphenyle, leur procede de preparation et leur utilisation comme medicaments
DE2633679A1 (de)	1977-02-17	4,5-dihydro-2-niederalkoxycarbonylamino-4-phenylimidazole und derivate davon mit substituierter phenylgruppe
EP0411735B1 (fr)	1995-05-17	Cycloalkylène-azoles, leur procédé de préparation, formes pharmaceutiques les contenant ainsi que leur application à la préparation de médicaments
DE2738640A1 (de)	1978-03-02	Herbizide triazolyl -und imidazolylverbindungen
US3987189A (en)	1976-10-19	Anti-inflammatory composition and method containing cyclic 2-furfural-acetals
CH618438A5 (fr)	1980-07-31
WO1996023790A1 (fr)	1996-08-08	Acetylimidazobenzodiazepines
DE2242454A1 (de)	1974-03-07	1-aethyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2242059A1 (de)	1973-03-15	2,4-dihydro-1h-s-triazolo eckige klammer auf 4,3-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepine und verfahren zu ihrer herstellung
CH618687A5 (fr)	1980-08-15
DE2812366A1 (de)	1978-10-05	Oxyalkansaeurederivate, verfahren zu ihrer herstellung und solche derivate enthaltende pharmazeutische zusammensetzungen
EP0298921A1 (fr)	1989-01-11	1,2-Benzisoxazoles et 1,2-benzisothiazoles
EP0057863A2 (fr)	1982-08-18	Agent antimicrobien
US3992400A (en)	1976-11-16	1-(α-Phenyl-o-tolyl)imidazoles
EP0045521B1 (fr)	1984-06-27	Pyrazolobenzazépines, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0130151A1 (fr)	1985-01-02	Dérivés du benzofuranne substitué en position 2