CH615660A5 - Esterification process - Google Patents
Esterification process Download PDFInfo
- Publication number
- CH615660A5 CH615660A5 CH632178A CH1368777A CH615660A5 CH 615660 A5 CH615660 A5 CH 615660A5 CH 632178 A CH632178 A CH 632178A CH 1368777 A CH1368777 A CH 1368777A CH 615660 A5 CH615660 A5 CH 615660A5
- Authority
- CH
- Switzerland
- Prior art keywords
- benzotriazole
- substituted
- group
- chloro
- mixture
- Prior art date
Links
- 238000005886 esterification reaction Methods 0.000 title claims abstract description 20
- 230000032050 esterification Effects 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 17
- -1 carboxyl compound Chemical class 0.000 claims abstract description 271
- 230000002378 acidificating effect Effects 0.000 claims abstract description 18
- 125000000962 organic group Chemical group 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- 238000007086 side reaction Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 119
- 125000000623 heterocyclic group Chemical group 0.000 claims description 86
- 239000012964 benzotriazole Substances 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000001931 aliphatic group Chemical group 0.000 claims description 39
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 26
- 125000002950 monocyclic group Chemical group 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- VGRXAHXMIDCTNV-UHFFFAOYSA-N (6-chlorobenzotriazol-1-yl) 4-chlorobenzenesulfonate Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)ON1C2=CC(Cl)=CC=C2N=N1 VGRXAHXMIDCTNV-UHFFFAOYSA-N 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 11
- YWOKHWQFDZLIOA-UHFFFAOYSA-N ethyl 2-cyano-2-methylsulfonyloxyiminoacetate Chemical compound CCOC(=O)C(C#N)=NOS(C)(=O)=O YWOKHWQFDZLIOA-UHFFFAOYSA-N 0.000 claims description 9
- RVFMZBYPSSUAAR-UHFFFAOYSA-N benzotriazol-1-yl methanesulfonate Chemical compound C1=CC=C2N(OS(=O)(=O)C)N=NC2=C1 RVFMZBYPSSUAAR-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- AZYZDWOTYBTZQO-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) methanesulfonate Chemical compound CS(=O)(=O)ON1C(=O)CCC1=O AZYZDWOTYBTZQO-UHFFFAOYSA-N 0.000 claims description 6
- OEZJBEZLNLHUIE-UHFFFAOYSA-N (4-chlorobenzotriazol-1-yl) methanesulfonate Chemical compound C1=CC=C2N(OS(=O)(=O)C)N=NC2=C1Cl OEZJBEZLNLHUIE-UHFFFAOYSA-N 0.000 claims description 6
- PZOIHJMCQFTWSK-UHFFFAOYSA-N (6-chlorobenzotriazol-1-yl) benzenesulfonate Chemical compound C12=CC(Cl)=CC=C2N=NN1OS(=O)(=O)C1=CC=CC=C1 PZOIHJMCQFTWSK-UHFFFAOYSA-N 0.000 claims description 6
- NLVZWRHEPVGDNM-UHFFFAOYSA-N (6-chlorobenzotriazol-1-yl) phenylmethanesulfonate Chemical compound C12=CC(Cl)=CC=C2N=NN1OS(=O)(=O)CC1=CC=CC=C1 NLVZWRHEPVGDNM-UHFFFAOYSA-N 0.000 claims description 6
- QFLQBALLSHEAQB-UHFFFAOYSA-N [(2-amino-1-cyano-2-oxoethylidene)amino] methanesulfonate Chemical compound CS(=O)(=O)ON=C(C#N)C(N)=O QFLQBALLSHEAQB-UHFFFAOYSA-N 0.000 claims description 6
- VZCUEBMBHOCUAE-UHFFFAOYSA-N ethyl 2-cyano-2-(4-methylphenyl)sulfonyloxyiminoacetate Chemical compound CCOC(=O)C(C#N)=NOS(=O)(=O)C1=CC=C(C)C=C1 VZCUEBMBHOCUAE-UHFFFAOYSA-N 0.000 claims description 6
- NVGWBFALHHJDOD-UHFFFAOYSA-N (4-oxo-1,2,3-benzotriazin-3-yl) benzenesulfonate Chemical compound N1=NC2=CC=CC=C2C(=O)N1OS(=O)(=O)C1=CC=CC=C1 NVGWBFALHHJDOD-UHFFFAOYSA-N 0.000 claims description 5
- MTXDVXJXKQJRHR-UHFFFAOYSA-N (6-chlorobenzotriazol-1-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON1C2=CC(Cl)=CC=C2N=N1 MTXDVXJXKQJRHR-UHFFFAOYSA-N 0.000 claims description 5
- JUCGHZYGCQMMKN-UHFFFAOYSA-N (6-chlorobenzotriazol-1-yl) butane-1-sulfonate Chemical compound C1=C(Cl)C=C2N(OS(=O)(=O)CCCC)N=NC2=C1 JUCGHZYGCQMMKN-UHFFFAOYSA-N 0.000 claims description 5
- XDPOGZLTCRXZHG-UHFFFAOYSA-N (6-chlorobenzotriazol-1-yl) methanesulfonate Chemical compound C1=C(Cl)C=C2N(OS(=O)(=O)C)N=NC2=C1 XDPOGZLTCRXZHG-UHFFFAOYSA-N 0.000 claims description 5
- IXLKXJHSJPJDOG-UHFFFAOYSA-N (6-ethenylbenzotriazol-1-yl) 4-chlorobenzenesulfonate Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)ON1C2=CC(C=C)=CC=C2N=N1 IXLKXJHSJPJDOG-UHFFFAOYSA-N 0.000 claims description 5
- IVOJAGDUDJMOJS-UHFFFAOYSA-N (6-ethenylbenzotriazol-1-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON1C2=CC(C=C)=CC=C2N=N1 IVOJAGDUDJMOJS-UHFFFAOYSA-N 0.000 claims description 5
- HMRIVNOLYSKMPV-UHFFFAOYSA-N (6-ethenylbenzotriazol-1-yl) methanesulfonate Chemical compound C1=C(C=C)C=C2N(OS(=O)(=O)C)N=NC2=C1 HMRIVNOLYSKMPV-UHFFFAOYSA-N 0.000 claims description 5
- IATHBTTWWJRUOM-UHFFFAOYSA-N (6-nitrobenzotriazol-1-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON1C2=CC([N+]([O-])=O)=CC=C2N=N1 IATHBTTWWJRUOM-UHFFFAOYSA-N 0.000 claims description 5
- QUHNLGFKKSMGQM-UHFFFAOYSA-N (6-nitrobenzotriazol-1-yl) benzenesulfonate Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=NN1OS(=O)(=O)C1=CC=CC=C1 QUHNLGFKKSMGQM-UHFFFAOYSA-N 0.000 claims description 5
- CRZSYUDQEGWSNO-UHFFFAOYSA-N benzotriazol-1-yl butane-1-sulfonate Chemical compound C1=CC=C2N(OS(=O)(=O)CCCC)N=NC2=C1 CRZSYUDQEGWSNO-UHFFFAOYSA-N 0.000 claims description 5
- FQRVJJXBEDWEFR-UHFFFAOYSA-N benzotriazol-1-yl pyridine-3-sulfonate Chemical compound N1=NC2=CC=CC=C2N1OS(=O)(=O)C1=CC=CN=C1 FQRVJJXBEDWEFR-UHFFFAOYSA-N 0.000 claims description 5
- SIIRMGYAJOOPNM-UHFFFAOYSA-N (2-oxo-3-phenylbenzimidazol-1-yl) methanesulfonate Chemical compound O=C1N(OS(=O)(=O)C)C2=CC=CC=C2N1C1=CC=CC=C1 SIIRMGYAJOOPNM-UHFFFAOYSA-N 0.000 claims description 4
- YKMVNWHIWOJKBD-UHFFFAOYSA-N (4-oxo-1,2,3-benzotriazin-3-yl) methanesulfonate Chemical compound C1=CC=C2C(=O)N(OS(=O)(=O)C)N=NC2=C1 YKMVNWHIWOJKBD-UHFFFAOYSA-N 0.000 claims description 4
- ARHXMQMZLUSMOG-UHFFFAOYSA-N (6-ethenylbenzotriazol-1-yl) ethenesulfonate Chemical compound C=CC1=CC=C2N=NN(OS(=O)(=O)C=C)C2=C1 ARHXMQMZLUSMOG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- DIBYYVCCWAYUOS-UHFFFAOYSA-N benzotriazol-1-yl 2-phenylethenesulfonate Chemical compound N1=NC2=CC=CC=C2N1OS(=O)(=O)C=CC1=CC=CC=C1 DIBYYVCCWAYUOS-UHFFFAOYSA-N 0.000 claims description 4
- JFPIODIIWKKJAZ-UHFFFAOYSA-N benzotriazol-1-yl benzenesulfonate Chemical compound N1=NC2=CC=CC=C2N1OS(=O)(=O)C1=CC=CC=C1 JFPIODIIWKKJAZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- JOGDTUSETDERGC-UHFFFAOYSA-N (2-oxo-3-phenylbenzimidazol-1-yl) 4-chlorobenzenesulfonate Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)ON1C(=O)N(C=2C=CC=CC=2)C2=CC=CC=C21 JOGDTUSETDERGC-UHFFFAOYSA-N 0.000 claims description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical compound C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 claims description 3
- FJOOVXJGNSEIKR-UHFFFAOYSA-N benzotriazol-1-yl 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)ON1C2=CC=CC=C2N=N1 FJOOVXJGNSEIKR-UHFFFAOYSA-N 0.000 claims description 3
- NRSFVZCITXLCFA-UHFFFAOYSA-N benzotriazol-1-yl 4-chlorobenzenesulfonate Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)ON1C2=CC=CC=C2N=N1 NRSFVZCITXLCFA-UHFFFAOYSA-N 0.000 claims description 3
- BLBFIFDDXNMRFP-UHFFFAOYSA-N benzotriazol-1-yl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON1C2=CC=CC=C2N=N1 BLBFIFDDXNMRFP-UHFFFAOYSA-N 0.000 claims description 3
- SZEQTDRKNONJNO-UHFFFAOYSA-N benzotriazol-1-yl 4-nitrobenzenesulfonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)ON1C2=CC=CC=C2N=N1 SZEQTDRKNONJNO-UHFFFAOYSA-N 0.000 claims description 3
- NQKRHEYQLFFZMB-UHFFFAOYSA-N benzotriazol-1-yl phenylmethanesulfonate Chemical compound N1=NC2=CC=CC=C2N1OS(=O)(=O)CC1=CC=CC=C1 NQKRHEYQLFFZMB-UHFFFAOYSA-N 0.000 claims description 3
- 201000004624 Dermatitis Diseases 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000005171 halobenzenes Chemical class 0.000 claims description 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 231
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 141
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 135
- 239000000203 mixture Substances 0.000 description 110
- 238000002844 melting Methods 0.000 description 83
- 230000008018 melting Effects 0.000 description 83
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 79
- 239000013078 crystal Substances 0.000 description 52
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- 239000002904 solvent Substances 0.000 description 46
- 125000001424 substituent group Chemical group 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 238000001816 cooling Methods 0.000 description 36
- 238000003756 stirring Methods 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- 125000002252 acyl group Chemical group 0.000 description 26
- 238000001035 drying Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 25
- 235000017557 sodium bicarbonate Nutrition 0.000 description 25
- 239000000284 extract Substances 0.000 description 18
- 239000003208 petroleum Substances 0.000 description 18
- 229910052717 sulfur Inorganic materials 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 13
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 13
- 125000004430 oxygen atom Chemical group O* 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 125000004434 sulfur atom Chemical group 0.000 description 11
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000005425 toluyl group Chemical group 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000002211 ultraviolet spectrum Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 125000005023 xylyl group Chemical group 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 4
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- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005024 alkenyl aryl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- CENQUTVRMPTFCN-UHFFFAOYSA-N benzotriazol-1-yl benzoate Chemical compound N1=NC2=CC=CC=C2N1OC(=O)C1=CC=CC=C1 CENQUTVRMPTFCN-UHFFFAOYSA-N 0.000 description 1
- PPFATIBRDZBCEH-UHFFFAOYSA-N benzotriazol-1-yl ethenesulfonate Chemical compound C1=CC=C2N(OS(=O)(=O)C=C)N=NC2=C1 PPFATIBRDZBCEH-UHFFFAOYSA-N 0.000 description 1
- 125000004935 benzoxazolinyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- QQSJOAMGJGHUCS-UHFFFAOYSA-N benzyl 2-(tetrazol-1-yl)acetate Chemical compound C=1C=CC=CC=1COC(=O)CN1C=NN=N1 QQSJOAMGJGHUCS-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000006640 cycloheptyl carbonyl group Chemical group 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
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YOJAHJGBFDPSDI-UHFFFAOYSA-N methyl 4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1 YOJAHJGBFDPSDI-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 125000005882 oxadiazolinyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005305 thiadiazolinyl group Chemical group 0.000 description 1
- 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/10—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using coupling agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2586674A JPS5748534B2 (enrdf_load_stackoverflow) | 1974-03-04 | 1974-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615660A5 true CH615660A5 (en) | 1980-02-15 |
Family
ID=12177709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH632178A CH615660A5 (en) | 1974-03-04 | 1974-04-26 | Esterification process |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5748534B2 (enrdf_load_stackoverflow) |
| CH (1) | CH615660A5 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002072564A1 (fr) * | 2001-03-12 | 2002-09-19 | Ono Pharmaceutical Co., Ltd. | Compose de n-phenylarylsulfonamide, medicament contenant le compose en tant que principe actif, intermediaire pour le compose et ses procedes de production |
-
1974
- 1974-03-04 JP JP2586674A patent/JPS5748534B2/ja not_active Expired
- 1974-04-26 CH CH632178A patent/CH615660A5/de not_active IP Right Cessation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002072564A1 (fr) * | 2001-03-12 | 2002-09-19 | Ono Pharmaceutical Co., Ltd. | Compose de n-phenylarylsulfonamide, medicament contenant le compose en tant que principe actif, intermediaire pour le compose et ses procedes de production |
| EP1612208A3 (en) * | 2001-03-12 | 2006-12-06 | Ono Pharmaceutical Co., Ltd. | N-phenylarylsulfonamide compound, pharmaceutical composition comprising the compound as active ingredient, synthetic intermediate for the compound and process for its preparation |
| RU2299202C2 (ru) * | 2001-03-12 | 2007-05-20 | Оно Фармасьютикал Ко., Лтд. | N-фениларилсульфонамид, фармацевтическая композиция, содержащая указанное соединение в качестве активного ингредиента, соединение, являющееся промежуточным в синтезе указанного соединения, и способ его получения |
| US7235667B2 (en) | 2001-03-12 | 2007-06-26 | Ono Pharmaceutical Co., Ltd. | N-phenylarylsulfonamide compound, pharmaceutical composition comprising the compound as active ingredient, synthetic intermediate for the compound and process for its preparation |
| US7629369B2 (en) | 2001-03-12 | 2009-12-08 | Ono Pharmaceuticals Co., Ltd. | N-phenylarylsulfonamide compound, pharmaceutical composition comprising the compound as active ingredient, synthetic intermediate for the compound and process for its preparation |
| US8088802B2 (en) | 2001-03-12 | 2012-01-03 | Ono Pharmaceutical Co., Ltd. | N-phenylarylsulfonamide compound, pharmaceutical composition comprising the compound as active ingredient, synthetic intermediate for the compound and process for its preparation |
| CZ304035B6 (cs) * | 2001-03-12 | 2013-08-28 | Ono Pharmaceutical Co., Ltd. | N-fenylarylsulfonamidová sloucenina, farmaceutická kompozice obsahující tuto slouceninu jako úcinnou slozku, syntetický meziprodukt pro tuto slouceninu a zpusob jeho prípravy |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5748534B2 (enrdf_load_stackoverflow) | 1982-10-16 |
| JPS50117711A (enrdf_load_stackoverflow) | 1975-09-16 |
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