NO327975B1 - Fremstilling av 4-tioalkyl-brombenzen-derivater - Google Patents
Fremstilling av 4-tioalkyl-brombenzen-derivater Download PDFInfo
- Publication number
- NO327975B1 NO327975B1 NO20030212A NO20030212A NO327975B1 NO 327975 B1 NO327975 B1 NO 327975B1 NO 20030212 A NO20030212 A NO 20030212A NO 20030212 A NO20030212 A NO 20030212A NO 327975 B1 NO327975 B1 NO 327975B1
- Authority
- NO
- Norway
- Prior art keywords
- sub
- methylthio
- dihydroisoxazol
- alkyl
- sup
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims abstract description 10
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- -1 C1-C6-halogenoalkyl Chemical group 0.000 claims description 98
- 238000000034 method Methods 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- 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 claims description 5
- 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 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 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
- OHPNRDSBFUZZFX-UHFFFAOYSA-N 3-(3-bromo-2-ethoxy-6-methylsulfanylphenyl)-4,5-dihydro-1,2-oxazole;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.CCOC1=C(Br)C=CC(SC)=C1C1=NOCC1 OHPNRDSBFUZZFX-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
- SJNSTLHRXGWUNM-UHFFFAOYSA-N CSC1=C(C(=C(C=C1)Br)C)C#N.CSC1=C(C=C(C=C1)Br)C#N Chemical compound CSC1=C(C(=C(C=C1)Br)C)C#N.CSC1=C(C=C(C=C1)Br)C#N SJNSTLHRXGWUNM-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 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 6
- 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
- 238000000746 purification Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000460 chlorine Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000012043 crude product Substances 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
- 150000002826 nitrites Chemical class 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
- 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
- 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
- 239000012414 tert-butyl nitrite Substances 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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- 125000004794 2-chloro-2-fluoroethoxy group Chemical group ClC(CO*)F 0.000 description 2
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 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
- 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
- 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
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 2
- 238000009776 industrial production Methods 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
- 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
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 239000004304 potassium nitrite Substances 0.000 description 2
- 235000010289 potassium nitrite Nutrition 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-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
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- FAFQZAMHELSOOA-UHFFFAOYSA-N 2-nitrosooxyethyl nitrite Chemical compound O=NOCCON=O FAFQZAMHELSOOA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QYYVZLSLIRDNBT-UHFFFAOYSA-N 3-(3-bromo-2-ethoxy-6-methylsulfanylphenyl)-5-methyl-1,2-oxazole Chemical compound CCOC1=C(Br)C=CC(SC)=C1C1=NOC(C)=C1 QYYVZLSLIRDNBT-UHFFFAOYSA-N 0.000 description 1
- MNQSNLGISSLYLN-UHFFFAOYSA-N 3-(3-bromo-2-ethyl-6-methylsulfanylphenyl)-1,2-oxazole Chemical compound CCC1=C(Br)C=CC(SC)=C1C1=NOC=C1 MNQSNLGISSLYLN-UHFFFAOYSA-N 0.000 description 1
- AKDSINVRRBSGHE-UHFFFAOYSA-N 3-(3-bromo-2-ethyl-6-methylsulfanylphenyl)-4,5-dihydro-1,2-oxazole Chemical compound CCC1=C(Br)C=CC(SC)=C1C1=NOCC1 AKDSINVRRBSGHE-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- NSVQWXUDGBQYRG-UHFFFAOYSA-N 3-(3-bromo-2-methoxy-6-methylsulfanylphenyl)-5-methyl-1,2-oxazole Chemical compound COC1=C(Br)C=CC(SC)=C1C1=NOC(C)=C1 NSVQWXUDGBQYRG-UHFFFAOYSA-N 0.000 description 1
- RNTFCJTYAILLSR-UHFFFAOYSA-N 3-(3-bromo-2-methyl-6-methylsulfanylphenyl)-5-methyl-1,2-oxazole Chemical compound CSC1=CC=C(Br)C(C)=C1C1=NOC(C)=C1 RNTFCJTYAILLSR-UHFFFAOYSA-N 0.000 description 1
- HEPOMXCPXPQLEJ-UHFFFAOYSA-N 3-bromo-2-methyl-6-methylsulfanylbenzonitrile Chemical compound CSC1=CC=C(Br)C(C)=C1C#N HEPOMXCPXPQLEJ-UHFFFAOYSA-N 0.000 description 1
- FFLMNCXMIQWPEO-UHFFFAOYSA-N 5-bromo-2-methylsulfanylbenzonitrile Chemical compound CSC1=CC=C(Br)C=C1C#N FFLMNCXMIQWPEO-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- 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
- 125000004123 n-propyl group Chemical group [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
- 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
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10035075 | 2000-07-17 | ||
| PCT/EP2001/008238 WO2002006211A1 (en) | 2000-07-17 | 2001-07-17 | Preparation of 4-thioalkylbromobenzene derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030212L NO20030212L (no) | 2003-01-16 |
| NO20030212D0 NO20030212D0 (no) | 2003-01-16 |
| NO327975B1 true NO327975B1 (no) | 2009-11-02 |
Family
ID=7649445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030212A NO327975B1 (no) | 2000-07-17 | 2003-01-16 | Fremstilling av 4-tioalkyl-brombenzen-derivater |
Country Status (22)
| Country | Link |
|---|---|
| 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) | AU2001287633B2 (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) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK287967B6 (sk) * | 1998-05-11 | 2012-07-03 | Basf Aktiengesellschaft | Process for preparing benzaldoximes |
| US8927551B2 (en) | 2009-05-18 | 2015-01-06 | 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 |
| US9149465B2 (en) | 2009-05-18 | 2015-10-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| AR081526A1 (es) | 2010-03-23 | 2012-10-03 | Basf Se | Piridazinas sustituidas que tienen accion herbicida |
| EP2550271A1 (de) | 2010-03-23 | 2013-01-30 | Basf Se | Substituierte pyridine mit herbizider wirkung |
| JP2013522335A (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 | 除草活性を有するピラジノチアジン |
| MX2012010454A (es) | 2010-03-23 | 2012-10-03 | Basf Se | Piridinas 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 |
| 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 |
| CA2818897A1 (en) | 2010-12-23 | 2012-06-28 | Basf Se | Substituted pyridines having herbicidal activity |
| WO2012168241A1 (en) | 2011-06-09 | 2012-12-13 | Basf Se | Substituted pyrazines having herbicidal activity |
| JP2014517000A (ja) | 2011-06-09 | 2014-07-17 | 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 |
| EP3266457A1 (de) | 2011-10-28 | 2018-01-10 | Lumena Pharmaceuticals LLC | Gallensäurerückflusshemmer zur behandlung von cholestase-erkrankungen im kindesalter |
| EP2855485A1 (de) | 2012-06-01 | 2015-04-08 | Basf Se | Substituierte pyridinverbindungen mit herbizidwirkung |
| CN105246900A (zh) | 2013-05-24 | 2016-01-13 | 巴斯夫欧洲公司 | 具有除草活性的取代吡啶化合物 |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9310203D0 (en) * | 1993-05-18 | 1993-06-30 | Rhone Poulenc Agriculture | Compositions of new matter |
| EE05455B1 (et) | 1997-01-17 | 2011-08-15 | Basf Aktiengesellschaft | 3-heterotskll-asendatud bensolderivaadid ja neid sisaldavad vahendid, nende saamise meetodid ning nende kasutamine herbitsiididena |
| SK287967B6 (sk) * | 1998-05-11 | 2012-07-03 | Basf Aktiengesellschaft | Process for preparing benzaldoximes |
| 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 AU AU2001287633A patent/AU2001287633B2/en not_active Ceased
- 2001-07-17 KR KR1020037000657A patent/KR100729324B1/ko not_active IP Right Cessation
- 2001-07-17 MX MXPA03000235A patent/MXPA03000235A/es active IP Right Grant
- 2001-07-17 US US10/332,861 patent/US7301034B2/en not_active Expired - Lifetime
- 2001-07-17 SK SK46-2003A patent/SK286986B6/sk not_active IP Right Cessation
- 2001-07-17 DK DK01967194T patent/DK1301469T3/da active
- 2001-07-17 NZ NZ524049A patent/NZ524049A/en unknown
- 2001-07-17 WO PCT/EP2001/008238 patent/WO2002006211A1/en active IP Right Grant
- 2001-07-17 JP JP2002512117A patent/JP4990472B2/ja not_active Expired - Lifetime
- 2001-07-17 EA EA200300100A patent/EA007931B1/ru not_active IP Right Cessation
- 2001-07-17 AU AU8763301A patent/AU8763301A/xx active Pending
- 2001-07-17 CZ CZ2003130A patent/CZ2003130A3/cs unknown
- 2001-07-17 BR BRPI0112530-3A patent/BR0112530B1/pt not_active IP Right Cessation
- 2001-07-17 HU HU0301724A patent/HUP0301724A2/hu unknown
- 2001-07-17 IL IL15351901A patent/IL153519A0/xx active IP Right Grant
- 2001-07-17 DE DE60120979T patent/DE60120979T2/de not_active Expired - Lifetime
- 2001-07-17 AT AT01967194T patent/ATE330936T1/de active
- 2001-07-17 EP EP01967194A patent/EP1301469B1/de not_active Expired - Lifetime
- 2001-07-17 CN CNB018129129A patent/CN1210269C/zh not_active Expired - Lifetime
- 2001-07-17 ES ES01967194T patent/ES2266246T3/es not_active Expired - Lifetime
- 2001-07-17 CA CA002416722A patent/CA2416722A1/en not_active Abandoned
-
2003
- 2003-01-16 NO NO20030212A patent/NO327975B1/no not_active IP Right Cessation
- 2003-02-14 ZA ZA200301220A patent/ZA200301220B/en unknown
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Legal Events
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| MM1K | Lapsed by not paying the annual fees |