ZA200301220B - Preparation of 4-thioalkylbromobenzene derivatives. - Google Patents

Preparation of 4-thioalkylbromobenzene derivatives. Download PDF

Info

Publication number: ZA200301220B
Authority: ZA; South Africa
Prior art keywords: methylthio; dihydroisoxazol; alkyl; formula; methyl
Prior art date: 2000-07-17

Application number

ZA200301220A

Other languages

English (en)

Inventor

Joachim Gebhardt

Michael Keil

Rene Lochtman

Michael Rack

Wolfgang Von Deyn

Original Assignee

Basf Ag

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.)

2000-07-17

Filing date

2003-02-14

Publication date

2004-02-25

2003-02-14 Application filed by Basf Ag filed Critical Basf Ag

2004-02-25 Publication of ZA200301220B publication Critical patent/ZA200301220B/en

Links

238000002360 preparation method Methods 0.000 title claims description 9
-1 5-methylisoxazol-3-yl Chemical group 0.000 claims description 80
238000000034 method Methods 0.000 claims description 38
150000001875 compounds Chemical class 0.000 claims description 37
238000006243 chemical reaction Methods 0.000 claims description 27
239000002904 solvent Substances 0.000 claims description 21
239000003054 catalyst Substances 0.000 claims description 17
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 12
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 10
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
235000010288 sodium nitrite Nutrition 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000003965 isoxazolidinyl group Chemical group 0.000 claims description 3
QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 3
BJKHEGMQFCIUHE-UHFFFAOYSA-N 3-(3-bromo-2-methyl-6-methylsulfanylphenyl)-4,5-dihydro-1,2-oxazole Chemical compound CSC1=CC=C(Br)C(C)=C1C1=NOCC1 BJKHEGMQFCIUHE-UHFFFAOYSA-N 0.000 claims description 2
FEHRYQNFBDUPHP-UHFFFAOYSA-N CSC1=C(C(=C(C=C1)Br)OC)C1=NOCC1.CSC1=C(C(=C(C=C1)Br)CC)C1=NOCC1.CSC1=C(C(=C(C=C1)Br)C)C1=NOCC1 Chemical compound CSC1=C(C(=C(C=C1)Br)OC)C1=NOCC1.CSC1=C(C(=C(C=C1)Br)CC)C1=NOCC1.CSC1=C(C(=C(C=C1)Br)C)C1=NOCC1 FEHRYQNFBDUPHP-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
ONYNVKOLQKKTEO-UHFFFAOYSA-N 3-(3-bromo-2-ethoxy-6-methylsulfanylphenyl)-1,2-oxazole Chemical compound CCOC1=C(Br)C=CC(SC)=C1C1=NOC=C1 ONYNVKOLQKKTEO-UHFFFAOYSA-N 0.000 claims 1
JKPDSBHEQVZLOJ-UHFFFAOYSA-N 3-(3-bromo-2-ethyl-6-methylsulfanylphenyl)-5-methyl-1,2-oxazole Chemical compound CCC1=C(Br)C=CC(SC)=C1C1=NOC(C)=C1 JKPDSBHEQVZLOJ-UHFFFAOYSA-N 0.000 claims 1
TXFOOPAUECCQJB-UHFFFAOYSA-N 3-(3-bromo-2-methoxy-6-methylsulfanylphenyl)-1,2-oxazole Chemical compound COC1=C(Br)C=CC(SC)=C1C1=NOC=C1 TXFOOPAUECCQJB-UHFFFAOYSA-N 0.000 claims 1
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 1
JQRUPGYAWZXJSL-UHFFFAOYSA-N 5-(3-bromo-2-methoxy-6-methylsulfanylphenyl)-3-methyl-4,5-dihydro-1,2-oxazole Chemical compound COC1=C(Br)C=CC(SC)=C1C1ON=C(C)C1 JQRUPGYAWZXJSL-UHFFFAOYSA-N 0.000 claims 1
PFXKBJVGWVDDEO-UHFFFAOYSA-N CSC1=C(C(=C(C=C1)Br)CC)C1=NOC=C1.CSC1=C(C(=C(C=C1)Br)C)C1=NOC=C1.CSC1=C(C(=C(C=C1)Br)OCC)C1CC(=NO1)C Chemical compound CSC1=C(C(=C(C=C1)Br)CC)C1=NOC=C1.CSC1=C(C(=C(C=C1)Br)C)C1=NOC=C1.CSC1=C(C(=C(C=C1)Br)OCC)C1CC(=NO1)C PFXKBJVGWVDDEO-UHFFFAOYSA-N 0.000 claims 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 15
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
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 5
238000000605 extraction Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000460 chlorine Chemical group 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
150000002019 disulfides Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
238000005406 washing Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
229960003116 amyl nitrite Drugs 0.000 description 3
239000012043 crude product Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 3
150000002826 nitrites Chemical class 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 3
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 2
125000005999 2-bromoethyl group Chemical group 0.000 description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 2
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
ICMSGNRMZFNBLN-UHFFFAOYSA-N 4-bromo-2-(4,5-dihydro-1,2-oxazol-3-yl)-3-methylaniline Chemical compound CC1=C(Br)C=CC(N)=C1C1=NOCC1 ICMSGNRMZFNBLN-UHFFFAOYSA-N 0.000 description 2
AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 2
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 2
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 2
125000006006 difluoroethoxy group Chemical group 0.000 description 2
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
125000006343 heptafluoro propyl group Chemical group 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000003971 isoxazolinyl group Chemical group 0.000 description 2
125000000842 isoxazolyl group Chemical group 0.000 description 2
239000000155 melt Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000004304 potassium nitrite Substances 0.000 description 2
235000010289 potassium nitrite Nutrition 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
125000006413 ring segment Chemical group 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
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 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
PTMWHLLVRFUEGT-UHFFFAOYSA-N 1-bromo-2-methyl-3,4-bis(methylsulfanyl)benzene Chemical compound CSC1=CC=C(Br)C(C)=C1SC PTMWHLLVRFUEGT-UHFFFAOYSA-N 0.000 description 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000004796 2,2-dichloro-2-fluoroethoxy group Chemical group ClC(CO*)(F)Cl 0.000 description 1
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
WFHOMNTZZFXZJC-UHFFFAOYSA-N 5-(3-bromo-2-methyl-6-methylsulfanylphenyl)-3-methyl-4,5-dihydro-1,2-oxazole Chemical compound CSC1=CC=C(Br)C(C)=C1C1ON=C(C)C1 WFHOMNTZZFXZJC-UHFFFAOYSA-N 0.000 description 1
QGMFOXKTIHHOMM-UHFFFAOYSA-N CSC1=C(C(=C(C=C1)Br)C)C#N.CSC1=C(C=C(C=C1)Br)C#N.CSC1=C(C(=C(C=C1)Br)OCC)C1=NOC(=C1)C.CSC1=C(C(=C(C=C1)Br)OC)C1=NOC(=C1)C Chemical compound CSC1=C(C(=C(C=C1)Br)C)C#N.CSC1=C(C=C(C=C1)Br)C#N.CSC1=C(C(=C(C=C1)Br)OCC)C1=NOC(=C1)C.CSC1=C(C(=C(C=C1)Br)OC)C1=NOC(=C1)C QGMFOXKTIHHOMM-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical group ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical class Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical class [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940083608 sodium hydroxide Drugs 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200301220A 2000-07-17 2003-02-14 Preparation of 4-thioalkylbromobenzene derivatives. ZA200301220B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10035075		2000-07-17

Publications (1)

Publication Number	Publication Date
ZA200301220B true ZA200301220B (en)	2004-02-25

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Application Number	Title	Priority Date	Filing Date
ZA200301220A ZA200301220B (en)	2000-07-17	2003-02-14	Preparation of 4-thioalkylbromobenzene derivatives.

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US (1)	US7301034B2 (de)
EP (1)	EP1301469B1 (de)
JP (1)	JP4990472B2 (de)
KR (1)	KR100729324B1 (de)
CN (1)	CN1210269C (de)
AT (1)	ATE330936T1 (de)
AU (2)	AU8763301A (de)
BR (1)	BR0112530B1 (de)
CA (1)	CA2416722A1 (de)
CZ (1)	CZ2003130A3 (de)
DE (1)	DE60120979T2 (de)
DK (1)	DK1301469T3 (de)
EA (1)	EA007931B1 (de)
ES (1)	ES2266246T3 (de)
HU (1)	HUP0301724A2 (de)
IL (1)	IL153519A0 (de)
MX (1)	MXPA03000235A (de)
NO (1)	NO327975B1 (de)
NZ (1)	NZ524049A (de)
SK (1)	SK286986B6 (de)
WO (1)	WO2002006211A1 (de)
ZA (1)	ZA200301220B (de)

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DK1852424T3 (da) *	1998-05-11	2012-07-23	Basf Se	Fremgangsmåde til fremstilling af isoxazolin-3-YL-acylbenzener
US8927551B2 (en)	2009-05-18	2015-01-06	Infinity Pharmaceuticals, Inc.	Isoxazolines as inhibitors of fatty acid amide hydrolase
US9149465B2 (en)	2009-05-18	2015-10-06	Infinity Pharmaceuticals, Inc.	Isoxazolines as inhibitors of fatty acid amide hydrolase
US8765735B2 (en)	2009-05-18	2014-07-01	Infinity Pharmaceuticals, Inc.	Isoxazolines as inhibitors of fatty acid amide hydrolase
BR112012023761A2 (pt)	2010-03-23	2015-10-06	Basf Se	piridina substituída de fórmula i, composto de fórmula i, composição e método para controle de vegetação indesejada
BR112012023935A2 (pt)	2010-03-23	2015-09-15	Basf Se	piridazina substituída da fórmula i, composto para fórmula i, composição e método para o controle de vegetação indesejada
WO2011117151A1 (en)	2010-03-23	2011-09-29	Basf Se	Pyrazinothiazines having herbicidal action
AR081526A1 (es)	2010-03-23	2012-10-03	Basf Se	Piridazinas sustituidas que tienen accion herbicida
JP2013522339A (ja)	2010-03-23	2013-06-13	ビーエーエスエフソシエタス・ヨーロピア	除草作用を有する置換されたピリジン
JP2013522340A (ja)	2010-03-23	2013-06-13	ビーエーエスエフソシエタス・ヨーロピア	除草作用を有する置換されたピリジン
JP2014501742A (ja)	2010-12-23	2014-01-23	ビーエーエスエフソシエタス・ヨーロピア	除草活性を有する置換ピリジン
BR112013030822A2 (pt)	2011-06-09	2016-08-16	Basf Se	composto de piridina substituída da fórmula i, composição e método para controlar a vegetação indesejada
WO2012168241A1 (en)	2011-06-09	2012-12-13	Basf Se	Substituted pyrazines having herbicidal activity
CN104023727B (zh)	2011-10-28	2017-04-05	鲁美纳医药公司	用于治疗小儿胆汁淤积性肝病的胆汁酸再循环抑制剂
BR112014029531A2 (pt)	2012-06-01	2017-06-27	Basf Se	composto de piridina, composição e método para controlar vegetação indesejada
BR112015021600A2 (pt)	2013-05-24	2017-07-18	Basf Se	composto de piridina, composição e método para o controle da vegetação indesejável
CN104710332B (zh) *	2015-02-17	2017-01-04	温州大学	一种烯基硫化物的制备方法
CN112694427B (zh) *	2019-10-23	2022-11-18	江西天宇化工有限公司	一种制备2,3-二甲基苯甲硫醚的方法
CN111170908B (zh) *	2020-01-09	2021-08-17	北京印刷学院	一种2，4-二甲基-3-甲磺酰基卤苯的合成方法

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Publication number	Priority date	Publication date	Assignee	Title
GB9310203D0 (en) *	1993-05-18	1993-06-30	Rhone Poulenc Agriculture	Compositions of new matter
DE59814338D1 (de)	1997-01-17	2009-03-12	Basf Se	3-heteroxyclyl-substituierte benzoylderivate
DK1852424T3 (da) *	1998-05-11	2012-07-23	Basf Se	Fremgangsmåde til fremstilling af isoxazolin-3-YL-acylbenzener
DE19852095A1 (de) *	1998-11-12	2000-05-18	Basf Ag	Verfahren zur Herstellung von 2-Alkyl-3-(4,5-dihydroisoxazol-3-yl)-acylbenzolen

2001
- 2001-07-17 JP JP2002512117A patent/JP4990472B2/ja not_active Expired - Lifetime
- 2001-07-17 HU HU0301724A patent/HUP0301724A2/hu unknown
- 2001-07-17 EP EP01967194A patent/EP1301469B1/de not_active Expired - Lifetime
- 2001-07-17 AT AT01967194T patent/ATE330936T1/de active
- 2001-07-17 EA EA200300100A patent/EA007931B1/ru not_active IP Right Cessation
- 2001-07-17 CZ CZ2003130A patent/CZ2003130A3/cs unknown
- 2001-07-17 SK SK46-2003A patent/SK286986B6/sk not_active IP Right Cessation
- 2001-07-17 US US10/332,861 patent/US7301034B2/en not_active Expired - Lifetime
- 2001-07-17 CA CA002416722A patent/CA2416722A1/en not_active Abandoned
- 2001-07-17 IL IL15351901A patent/IL153519A0/xx active IP Right Grant
- 2001-07-17 CN CNB018129129A patent/CN1210269C/zh not_active Expired - Lifetime
- 2001-07-17 DK DK01967194T patent/DK1301469T3/da active
- 2001-07-17 WO PCT/EP2001/008238 patent/WO2002006211A1/en not_active Ceased
- 2001-07-17 MX MXPA03000235A patent/MXPA03000235A/es active IP Right Grant
- 2001-07-17 DE DE60120979T patent/DE60120979T2/de not_active Expired - Lifetime
- 2001-07-17 KR KR1020037000657A patent/KR100729324B1/ko not_active Expired - Fee Related
- 2001-07-17 ES ES01967194T patent/ES2266246T3/es not_active Expired - Lifetime
- 2001-07-17 BR BRPI0112530-3A patent/BR0112530B1/pt not_active IP Right Cessation
- 2001-07-17 NZ NZ524049A patent/NZ524049A/en unknown
- 2001-07-17 AU AU8763301A patent/AU8763301A/xx active Pending
- 2001-07-17 AU AU2001287633A patent/AU2001287633B2/en not_active Ceased
2003
- 2003-01-16 NO NO20030212A patent/NO327975B1/no not_active IP Right Cessation
- 2003-02-14 ZA ZA200301220A patent/ZA200301220B/en unknown

Also Published As

Publication number	Publication date
EP1301469A1 (de)	2003-04-16
EA007931B1 (ru)	2007-02-27
BR0112530A (pt)	2003-07-01
CZ2003130A3 (cs)	2003-09-17
US7301034B2 (en)	2007-11-27
CA2416722A1 (en)	2002-01-24
WO2002006211A1 (en)	2002-01-24
NO20030212L (no)	2003-01-16
JP2004504292A (ja)	2004-02-12
NO20030212D0 (no)	2003-01-16
ATE330936T1 (de)	2006-07-15
EA200300100A1 (ru)	2003-06-26
MXPA03000235A (es)	2003-06-06
BR0112530B1 (pt)	2012-05-02
NZ524049A (en)	2004-09-24
HUP0301724A2 (hu)	2003-08-28
IL153519A0 (en)	2003-07-06
DE60120979D1 (de)	2006-08-03
JP4990472B2 (ja)	2012-08-01
US20030149276A1 (en)	2003-08-07
ES2266246T3 (es)	2007-03-01
KR20030029622A (ko)	2003-04-14
PL366050A1 (en)	2005-01-24
CN1443156A (zh)	2003-09-17
AU2001287633B2 (en)	2006-12-14
CN1210269C (zh)	2005-07-13
DE60120979T2 (de)	2006-11-16
KR100729324B1 (ko)	2007-06-15
NO327975B1 (no)	2009-11-02
SK286986B6 (sk)	2009-08-06
AU8763301A (en)	2002-01-30
DK1301469T3 (da)	2006-10-23
SK462003A3 (en)	2003-07-01
EP1301469B1 (de)	2006-06-21

Publication	Publication Date	Title
EP1301469B1 (de)	2006-06-21	Verfahren zur herstellung von 4-thioalkylbrombenzol derivaten
KR100604302B1 (ko)	2006-07-28	이소옥사졸린-3-일-아실벤젠의 제조 방법
AU2001287633A1 (en)	2002-05-02	Preparation of 4-thioalkylbromobenzene derivatives
KR100779315B1 (ko)	2007-11-27	4-브로모아닐린 유도체의 제조 방법
US6388135B1 (en)	2002-05-14	Preparation of 4-bromoaniline derivatives
WO2025233270A1 (en)	2025-11-13	A PROCESS FOR PREPARATION OF α-FLUOROALKYL CARBOXYLIC ACID ESTERS