CA1103684A - Procede pour la preparation de derives d'acides alcanoiques substitues 2-thio-2 - Google Patents

Procede pour la preparation de derives d'acides alcanoiques substitues 2-thio-2

Info

Publication number: CA1103684A
Authority: CA; Canada
Prior art keywords: formula; group; substituted; carbon atoms; alkyl group
Prior art date: 1977-08-18
Legal status (The legal status 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 status listed.): Expired

Application number

CA309,676A

Other languages

English (en)

Inventor

Kiyosi Kondo

Minoru Suda

Daiei Tunemoto

Akira Negishi

Kumiko Kishi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sagami Chemical Research Institute

Original Assignee

Sagami Chemical Research Institute

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.)

1977-08-18

Filing date

1978-08-18

Publication date

1981-06-23

1977-08-18 Priority claimed from JP9827177A external-priority patent/JPS5432437A/ja

1977-09-07 Priority claimed from JP10682677A external-priority patent/JPS5441867A/ja

1977-10-17 Priority claimed from JP12350677A external-priority patent/JPS5459246A/ja

1978-08-18 Application filed by Sagami Chemical Research Institute filed Critical Sagami Chemical Research Institute

1981-06-23 Application granted granted Critical

1981-06-23 Publication of CA1103684A publication Critical patent/CA1103684A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 24
238000004519 manufacturing process Methods 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 56
-1 substituted-phenyl group Chemical group 0.000 claims abstract description 51
238000000034 method Methods 0.000 claims abstract description 50
125000000217 alkyl group Chemical group 0.000 claims abstract description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 34
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
125000005843 halogen group Chemical group 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
239000002168 alkylating agent Substances 0.000 claims abstract description 12
229940100198 alkylating agent Drugs 0.000 claims abstract description 12
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 8
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 8
125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 6
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims abstract description 6
230000032050 esterification Effects 0.000 claims abstract description 6
238000005886 esterification reaction Methods 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
101100006371 Arabidopsis thaliana CHX3 gene Proteins 0.000 claims description 6
230000002152 alkylating effect Effects 0.000 claims description 6
230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
230000000694 effects Effects 0.000 abstract description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 abstract description 4
230000003389 potentiating effect Effects 0.000 abstract description 3
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract description 3
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 abstract description 2
229960000905 indomethacin Drugs 0.000 abstract description 2
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
229960004889 salicylic acid Drugs 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 23
239000000243 solution Substances 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 18
239000002585 base Substances 0.000 description 17
238000003756 stirring Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
238000010898 silica gel chromatography Methods 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 7
230000009467 reduction Effects 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
GEERKXVSWNZEQS-UHFFFAOYSA-N 2-(3-phenoxyphenyl)-2-phenylsulfanylacetic acid Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1C(C(=O)O)SC1=CC=CC=C1 GEERKXVSWNZEQS-UHFFFAOYSA-N 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
238000000862 absorption spectrum Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
235000011167 hydrochloric acid Nutrition 0.000 description 5
229960000443 hydrochloric acid Drugs 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
239000000126 substance Substances 0.000 description 5
NLOLDUOUSDMWGN-UHFFFAOYSA-N 2-(3-phenoxyphenyl)-2-phenylsulfanylpropanoic acid Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1C(C)(C(O)=O)SC1=CC=CC=C1 NLOLDUOUSDMWGN-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
230000003301 hydrolyzing effect Effects 0.000 description 4
CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 4
229950009183 ibufenac Drugs 0.000 description 4
VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 4
KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
150000008062 acetophenones Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
229950005228 bromoform Drugs 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
238000001103 continuous-wave nuclear magnetic resonance spectrum Methods 0.000 description 3
238000005262 decarbonization Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
FZCDBGYCFVKRDV-UHFFFAOYSA-N 1-(3-phenoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FZCDBGYCFVKRDV-UHFFFAOYSA-N 0.000 description 2
FVBSOBQMQOBCRU-UHFFFAOYSA-N 2,2,2-trichloro-1-[4-(2-methylpropyl)phenyl]ethanol Chemical compound ClC(C(O)C1=CC=C(C=C1)CC(C)C)(Cl)Cl FVBSOBQMQOBCRU-UHFFFAOYSA-N 0.000 description 2
QEYFYYSRHVDMNJ-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]-2-phenylsulfanylacetic acid Chemical compound C1(=CC=CC=C1)SC(C(=O)O)C1=CC=C(C=C1)CC(C)C QEYFYYSRHVDMNJ-UHFFFAOYSA-N 0.000 description 2
WKDHGFKPKDADCQ-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]-2-phenylsulfanylpropanoic acid Chemical compound C1(=CC=CC=C1)SC(C(=O)O)(C)C1=CC=C(C=C1)CC(C)C WKDHGFKPKDADCQ-UHFFFAOYSA-N 0.000 description 2
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
150000004651 carbonic acid esters Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
RDJGLLICXDHJDY-UHFFFAOYSA-N fenoprofen Chemical compound OC(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical class N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000002994 raw material Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DBGSRZSKGVSXRK-UHFFFAOYSA-N 1-[2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]acetyl]-3,6-dihydro-2H-pyridine-4-carboxylic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CCC(=CC1)C(=O)O DBGSRZSKGVSXRK-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
DQGIAFGTEPJSDU-UHFFFAOYSA-N 2-(2-methylpropylsulfanyl)-2-(3-phenoxyphenyl)acetic acid Chemical compound CC(C)CSC(C(O)=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 DQGIAFGTEPJSDU-UHFFFAOYSA-N 0.000 description 1
LEMRHTTWKDVQEI-UHFFFAOYSA-N 2-(3-phenoxyphenyl)acetic acid Chemical class OC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1 LEMRHTTWKDVQEI-UHFFFAOYSA-N 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
GATVIKZLVQHOMN-UHFFFAOYSA-N Chlorodibromomethane Chemical compound ClC(Br)Br GATVIKZLVQHOMN-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
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 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
FMWLUWPQPKEARP-UHFFFAOYSA-N bromodichloromethane Chemical compound ClC(Cl)Br FMWLUWPQPKEARP-UHFFFAOYSA-N 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
239000010410 layer Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
USXYVUYBWROVFR-UHFFFAOYSA-N methyl 2-(3-phenoxyphenyl)-2-phenylsulfanylpropanoate Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1C(C)(C(=O)OC)SC1=CC=CC=C1 USXYVUYBWROVFR-UHFFFAOYSA-N 0.000 description 1
FUOQIQZCJJDBGD-UHFFFAOYSA-N methyl 2-(3-phenoxyphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 FUOQIQZCJJDBGD-UHFFFAOYSA-N 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA309,676A 1977-08-18 1978-08-18 Procede pour la preparation de derives d'acides alcanoiques substitues 2-thio-2 Expired CA1103684A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP9827177A JPS5432437A (en)	1977-08-18	1977-08-18	2-thio-2-(3-phenoxyphenyl)alkane-carboxylic acid derivatives and their preparation
JP98271/77		1977-08-18
JP10682677A JPS5441867A (en)	1977-09-07	1977-09-07	Alpha-thio--alpha(2-thienyl)alkanoic acid derivative and its preparation
JP106826/77		1977-09-07
JP123506/77		1977-10-17
JP12350677A JPS5459246A (en)	1977-10-17	1977-10-17	2-thio-2-(4-isobutylphenyl) alkane acid derivatives and their preparation

Publications (1)

Publication Number	Publication Date
CA1103684A true CA1103684A (fr)	1981-06-23

Family

ID=27308618

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA309,676A Expired CA1103684A (fr)	1977-08-18	1978-08-18	Procede pour la preparation de derives d'acides alcanoiques substitues 2-thio-2

Country Status (4)

Country	Link
CA (1)	CA1103684A (fr)
DE (1)	DE2836257A1 (fr)
FR (1)	FR2400507A1 (fr)
GB (1)	GB2007220B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3700732A1 (de) *	1987-01-13	1988-07-21	Boehringer Mannheim Gmbh	Neue carbonsaeurederivate, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten
FR3158475B1 (fr)	2024-01-18	2026-05-01	Stellantis Auto Sas	Calandre lumineuse à éclairages indépendants, pour un véhicule

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3584056A (en) *	1967-03-13	1971-06-08	Procter & Gamble	Process for preparing alkali metal alkyl thiomethyl mercaptans by reaction of alkylthiomethylmetal compounds and sulfur

1978
- 1978-08-14 GB GB7833298A patent/GB2007220B/en not_active Expired
- 1978-08-18 DE DE19782836257 patent/DE2836257A1/de not_active Ceased
- 1978-08-18 CA CA309,676A patent/CA1103684A/fr not_active Expired
- 1978-08-18 FR FR7824142A patent/FR2400507A1/fr active Granted

Also Published As

Publication number	Publication date
GB2007220B (en)	1982-05-26
DE2836257A1 (de)	1979-03-01
FR2400507A1 (fr)	1979-03-16
FR2400507B1 (fr)	1984-07-27
GB2007220A (en)	1979-05-16

Legal Events

Date	Code	Title	Description
1998-06-23	MKEX	Expiry

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CA1103684A (fr)	1981-06-23	Procede pour la preparation de derives d'acides alcanoiques substitues 2-thio-2
EP0151702A2 (fr)	1985-08-21	Acétals de cétones alpha-hydroxylées
US4308208A (en)	1981-12-29	α-Methylthio-α-(p-phthalimidophenyl)-propionic acid
US4245108A (en)	1981-01-13	Process for preparing 2-thio-2-substituted-alkanoic acid derivatives
US4219659A (en)	1980-08-26	Process for the preparation of thiophene derivatives and thiophene derivatives obtained therethrough
JPH0770037A (ja)	1995-03-14	シアノアシルシクロプロパン化合物の製造方法とそれに用いる２−シアノアシル−４−ブタノリド化合物
US6235905B1 (en)	2001-05-22	Process for preparing alkoxypyrazine derivatives
USRE31260E (en)	1983-05-31	Process for the preparation of an acetonitrile derivative
US4247715A (en)	1981-01-27	2-Alkynyl-5-indanyloxyacetic acids
US4577025A (en)	1986-03-18	Method of preparing α-aromatic propionic acids and intermediates thereof
JPH05117263A (ja)	1993-05-14	３−アミノ−２−チオフエンカルボン酸誘導体の製造方法
US4131747A (en)	1978-12-26	Process for preparing α-substituted phenylalkanecarboxylic acid
US4155929A (en)	1979-05-22	Process for the preparation of an acetonitrile derivative
US4334088A (en)	1982-06-08	2-Alkynyl-5-indanyloxyacetic acids
US4340740A (en)	1982-07-20	Alpha-thio-alpha-aryl-substituted alkanonitrile and process for preparing alpha-aryl-substituted alkanonitrile therefrom
JP3777407B2 (ja)	2006-05-24	カルボン酸誘導体の製造法
EP0160241B1 (fr)	1988-11-30	Procédé de préparation d'un dérivé d'un acide alcanoylique substitué en position alpha par un groupe aromatique
JPH0210829B2 (fr)	1990-03-09
JPH07278047A (ja)	1995-10-24	アリールオキシプロピオン酸の製造法