BE557074A - - Google Patents
Info
- Publication number
- BE557074A BE557074A BE557074DA BE557074A BE 557074 A BE557074 A BE 557074A BE 557074D A BE557074D A BE 557074DA BE 557074 A BE557074 A BE 557074A
- Authority
- BE
- Belgium
- Prior art keywords
- radical
- carbon atoms
- sulfonyl
- urethane
- alkyl
- Prior art date
Links
- -1 alkali metal salts Chemical class 0.000 claims description 29
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 150000001298 alcohols Chemical class 0.000 claims description 14
- 239000011780 sodium chloride Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl N-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 230000000875 corresponding Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 229940093912 Gynecological Sulfonamides Drugs 0.000 claims description 5
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims description 5
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 229940026752 topical Sulfonamides Drugs 0.000 claims description 5
- 238000006136 alcoholysis reaction Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 47
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 159000000000 sodium salts Chemical class 0.000 description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 23
- 238000009835 boiling Methods 0.000 description 18
- 239000000155 melt Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 210000004369 Blood Anatomy 0.000 description 14
- 239000008280 blood Substances 0.000 description 14
- 239000003610 charcoal Substances 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000001184 potassium carbonate Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 6
- KIWBRXCOTCXSSZ-UHFFFAOYSA-N hexyl carbonochloridate Chemical compound CCCCCCOC(Cl)=O KIWBRXCOTCXSSZ-UHFFFAOYSA-N 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N 1-Hexanol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-N-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- BQBKYSPXQYHTIP-UHFFFAOYSA-N ethyl N-butylcarbamate Chemical compound CCCCNC(=O)OCC BQBKYSPXQYHTIP-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XAHONZKANMMOGS-UHFFFAOYSA-N C(CC(C)C)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound C(CC(C)C)S(=O)(=O)N(C(=O)OCC)CCCC XAHONZKANMMOGS-UHFFFAOYSA-N 0.000 description 3
- WTWDVBBHANGJOK-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC(C)C)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC(C)C)C WTWDVBBHANGJOK-UHFFFAOYSA-N 0.000 description 3
- YXTSNKIFXSHVFR-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)N(C(=O)OCC)CCCCCC Chemical compound C1(=CC=CC=C1)S(=O)(=O)N(C(=O)OCC)CCCCCC YXTSNKIFXSHVFR-UHFFFAOYSA-N 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N Phenethyl alcohol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- UAVOCTDYPKOULU-UHFFFAOYSA-N methylchloranuidyl formate Chemical compound C[Cl-]OC=O UAVOCTDYPKOULU-UHFFFAOYSA-N 0.000 description 3
- 230000001264 neutralization Effects 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- SETDGFFRAQQPBH-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC)C SETDGFFRAQQPBH-UHFFFAOYSA-N 0.000 description 2
- YPMFGPMFQZTXJD-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N(C(=O)OCC)CCCC YPMFGPMFQZTXJD-UHFFFAOYSA-N 0.000 description 2
- VYWRBAWFPGUTSI-UHFFFAOYSA-N CCCCCCN(C(=O)OCC)S(=O)(=O)CCC(C)C Chemical compound CCCCCCN(C(=O)OCC)S(=O)(=O)CCC(C)C VYWRBAWFPGUTSI-UHFFFAOYSA-N 0.000 description 2
- UTQBJRIDERVJQK-UHFFFAOYSA-N CCCCN(C(=O)OCC)S(=O)(=O)C1=CC(OC)=C(OC)C=C1 Chemical compound CCCCN(C(=O)OCC)S(=O)(=O)C1=CC(OC)=C(OC)C=C1 UTQBJRIDERVJQK-UHFFFAOYSA-N 0.000 description 2
- UUIZPHZFIIOUNE-UHFFFAOYSA-N COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC UUIZPHZFIIOUNE-UHFFFAOYSA-N 0.000 description 2
- 210000000936 Intestines Anatomy 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000003178 anti-diabetic Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003472 neutralizing Effects 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 230000001603 reducing Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HQRWWHIETAKIMO-UHFFFAOYSA-N 1-phenylbutan-1-ol Chemical class CCCC(O)C1=CC=CC=C1 HQRWWHIETAKIMO-UHFFFAOYSA-N 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N 1-phenylpropan-1-ol Chemical class CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-Pentanol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- IWEYZXWPWNBRLG-UHFFFAOYSA-N 2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(N)(=O)=O IWEYZXWPWNBRLG-UHFFFAOYSA-N 0.000 description 1
- GWJSQKNYHPYZRN-UHFFFAOYSA-N 2-methylpropane-2-sulfonamide Chemical compound CC(C)(C)S(N)(=O)=O GWJSQKNYHPYZRN-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- MEZNPUULYGXXFL-UHFFFAOYSA-N 3,4-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1OC MEZNPUULYGXXFL-UHFFFAOYSA-N 0.000 description 1
- MLTGAVXHWSDGIS-UHFFFAOYSA-N 4-ethylbenzenesulfonamide Chemical class CCC1=CC=C(S(N)(=O)=O)C=C1 MLTGAVXHWSDGIS-UHFFFAOYSA-N 0.000 description 1
- MSFQEZBRFPAFEX-UHFFFAOYSA-N 4-methoxybenzenesulfonamide Chemical class COC1=CC=C(S(N)(=O)=O)C=C1 MSFQEZBRFPAFEX-UHFFFAOYSA-N 0.000 description 1
- JVMQLNXAPHLKDV-UHFFFAOYSA-N 4-phenoxybenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1OC1=CC=CC=C1 JVMQLNXAPHLKDV-UHFFFAOYSA-N 0.000 description 1
- LDZLXQFDGRCELX-UHFFFAOYSA-N 4-phenylbutan-1-ol Chemical compound OCCCCC1=CC=CC=C1 LDZLXQFDGRCELX-UHFFFAOYSA-N 0.000 description 1
- WVOWEROKBOQYLJ-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonamide Chemical compound CC(C)C1=CC=C(S(N)(=O)=O)C=C1 WVOWEROKBOQYLJ-UHFFFAOYSA-N 0.000 description 1
- QTYDNBLDZCJBBC-UHFFFAOYSA-N C(C)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound C(C)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC QTYDNBLDZCJBBC-UHFFFAOYSA-N 0.000 description 1
- SGXHNBVJMTXCPY-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C(C)C)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C(C)C)C SGXHNBVJMTXCPY-UHFFFAOYSA-N 0.000 description 1
- KZQGKHFWQGKZKV-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCC)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCC)C KZQGKHFWQGKZKV-UHFFFAOYSA-N 0.000 description 1
- PWMYBXDPSGUJQM-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCCC)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCCC)C PWMYBXDPSGUJQM-UHFFFAOYSA-N 0.000 description 1
- NCIWGJSMUVSPPP-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCCCCCCCCC)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCCCCCCCCC)C NCIWGJSMUVSPPP-UHFFFAOYSA-N 0.000 description 1
- LHHHUPMFKLWKLA-UHFFFAOYSA-M C1(=CC=C(C=C1)S(=O)(=O)NC([O-])=O)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)S(=O)(=O)NC([O-])=O)C1=CC=CC=C1 LHHHUPMFKLWKLA-UHFFFAOYSA-M 0.000 description 1
- QJOMGHDTQWZPNC-UHFFFAOYSA-N CC=1C=C(C=CC1)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound CC=1C=C(C=CC1)S(=O)(=O)N(C(=O)OCC)CCCC QJOMGHDTQWZPNC-UHFFFAOYSA-N 0.000 description 1
- BTSODEYLXPCYNU-UHFFFAOYSA-N CCCCCCN(C(=O)OCC)S(=O)(=O)C1=CC(C)=C(C)C=C1 Chemical compound CCCCCCN(C(=O)OCC)S(=O)(=O)C1=CC(C)=C(C)C=C1 BTSODEYLXPCYNU-UHFFFAOYSA-N 0.000 description 1
- KWHXRPOBVUXTNC-UHFFFAOYSA-N COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C Chemical compound COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C KWHXRPOBVUXTNC-UHFFFAOYSA-N 0.000 description 1
- RQJRCKOLXHHTIW-UHFFFAOYSA-N COC1=CC=C(C=C1)S(=O)(=O)[NH-] Chemical compound COC1=CC=C(C=C1)S(=O)(=O)[NH-] RQJRCKOLXHHTIW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010012601 Diabetes mellitus Diseases 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N Dodecanol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N Isoamyl alcohol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LJVLPEBNLCAWRA-UHFFFAOYSA-N NS(=O)(=O)C1=CCCC1 Chemical compound NS(=O)(=O)C1=CCCC1 LJVLPEBNLCAWRA-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 210000002784 Stomach Anatomy 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N Sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N Tert-Amyl alcohol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001580 bacterial Effects 0.000 description 1
- YIYZHARUXWKUEN-UHFFFAOYSA-N benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1.NS(=O)(=O)C1=CC=CC=C1 YIYZHARUXWKUEN-UHFFFAOYSA-N 0.000 description 1
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- YEJJFGYKPOEVPJ-UHFFFAOYSA-N cycloheptanesulfonamide Chemical compound NS(=O)(=O)C1CCCCCC1 YEJJFGYKPOEVPJ-UHFFFAOYSA-N 0.000 description 1
- AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 description 1
- VJPGNAIPMMGCSU-UHFFFAOYSA-N cyclohexylmethanesulfonamide Chemical compound NS(=O)(=O)CC1CCCCC1 VJPGNAIPMMGCSU-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive Effects 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DFWQXANLGSXMKF-UHFFFAOYSA-N ethyl N-(4-methylphenyl)sulfonylcarbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 DFWQXANLGSXMKF-UHFFFAOYSA-N 0.000 description 1
- GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl N-ethylcarbamate Chemical class CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 description 1
- CXLBYPJSAWOYSI-UHFFFAOYSA-N ethyl N-methyl-N-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC=C(C)C=C1 CXLBYPJSAWOYSI-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000020828 fasting Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- XXRLNWSPPBSGMY-UHFFFAOYSA-N heptane-1-sulfonamide Chemical compound CCCCCCCS(N)(=O)=O XXRLNWSPPBSGMY-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- QWOKKHXWFDAJCZ-UHFFFAOYSA-N octane-1-sulfonamide Chemical compound CCCCCCCCS(N)(=O)=O QWOKKHXWFDAJCZ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases 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
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
- SJMCLWCCNYAWRQ-UHFFFAOYSA-N propane-2-sulfonamide Chemical compound CC(C)S(N)(=O)=O SJMCLWCCNYAWRQ-UHFFFAOYSA-N 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical compound OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical class CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE557074A true BE557074A (xx) |
Family
ID=180625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE557074D BE557074A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE557074A (xx) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4600792A (en) * | 1984-04-11 | 1986-07-15 | Nihon Tokushu Noyaku Seizo K.K. | Preparation of biphenylylsulfonylureas and intermediates therefor |
| US4612385A (en) * | 1984-12-06 | 1986-09-16 | Nihon Tokushu Noyaku Seizo K.K. | Process for the preparation of phenyl N-(2-biphenylylsulfonyl) carbamate |
-
0
- BE BE557074D patent/BE557074A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4600792A (en) * | 1984-04-11 | 1986-07-15 | Nihon Tokushu Noyaku Seizo K.K. | Preparation of biphenylylsulfonylureas and intermediates therefor |
| US4612385A (en) * | 1984-12-06 | 1986-09-16 | Nihon Tokushu Noyaku Seizo K.K. | Process for the preparation of phenyl N-(2-biphenylylsulfonyl) carbamate |
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