CH351589A - Verfahren zur Herstellung von Sulfonylharnstoffen - Google Patents
Verfahren zur Herstellung von SulfonylharnstoffenInfo
- Publication number
- CH351589A CH351589A CH351589DA CH351589A CH 351589 A CH351589 A CH 351589A CH 351589D A CH351589D A CH 351589DA CH 351589 A CH351589 A CH 351589A
- Authority
- CH
- Switzerland
- Prior art keywords
- urea
- benzenesulfonyl
- melting point
- salt
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- 229940100389 Sulfonylurea Drugs 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 phenoxyphenyl Chemical group 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000002844 melting Methods 0.000 description 62
- 230000008018 melting Effects 0.000 description 62
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 229910021529 ammonia Inorganic materials 0.000 description 20
- YBLWHGQKHHKWRU-UHFFFAOYSA-N 1,3-bis-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 YBLWHGQKHHKWRU-UHFFFAOYSA-N 0.000 description 19
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
- 235000013877 carbamide Nutrition 0.000 description 11
- 239000000155 melt Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- RUUGNIQERAFPSL-UHFFFAOYSA-N ethyl n-(benzenesulfonyl)carbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=CC=C1 RUUGNIQERAFPSL-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 5
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000003940 butylamines Chemical class 0.000 description 4
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- KUIYILOSSGJKHZ-UHFFFAOYSA-N 1,3-bis(benzenesulfonyl)urea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NS(=O)(=O)C1=CC=CC=C1 KUIYILOSSGJKHZ-UHFFFAOYSA-N 0.000 description 3
- HMTRNPUZXPJBFK-UHFFFAOYSA-N 1-cyclohexyl-3-cyclohexylsulfonylurea Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)NC1CCCCC1 HMTRNPUZXPJBFK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FKOAGWCOPBGKCQ-UHFFFAOYSA-N O=C(NS(C1CCCCC1)(=O)=O)NS(C1CCCCC1)(=O)=O Chemical compound O=C(NS(C1CCCCC1)(=O)=O)NS(C1CCCCC1)(=O)=O FKOAGWCOPBGKCQ-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 description 3
- 150000003946 cyclohexylamines Chemical class 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000003941 n-butylamines Chemical class 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 3
- BEEJXRDKFNZHFV-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-pentylurea Chemical compound CCCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 BEEJXRDKFNZHFV-UHFFFAOYSA-N 0.000 description 2
- QSLBKVNCTRJJNT-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-propylurea Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 QSLBKVNCTRJJNT-UHFFFAOYSA-N 0.000 description 2
- BNZMOMQBYDNFHM-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NS(=O)(=O)C1=CC=CC=C1 BNZMOMQBYDNFHM-UHFFFAOYSA-N 0.000 description 2
- FXXMUIOXUGJJKO-UHFFFAOYSA-N 1-butyl-3-(4-propan-2-ylphenyl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C(C)C)C=C1 FXXMUIOXUGJJKO-UHFFFAOYSA-N 0.000 description 2
- AQRJDVDPXATDJF-UHFFFAOYSA-N 1-hexyl-3-(4-methylphenyl)sulfonylurea Chemical compound CCCCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 AQRJDVDPXATDJF-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- MQBZVZWIESZJLM-UHFFFAOYSA-N CC(C)CNC(NS(C(C=C1)=CC(OC)=C1OC)(=O)=O)=O Chemical compound CC(C)CNC(NS(C(C=C1)=CC(OC)=C1OC)(=O)=O)=O MQBZVZWIESZJLM-UHFFFAOYSA-N 0.000 description 2
- ULZJFSDAGGMEOD-UHFFFAOYSA-N CC(C=C(C=C1)S(NC(NCC2CCCCC2)=O)(=O)=O)=C1OC Chemical compound CC(C=C(C=C1)S(NC(NCC2CCCCC2)=O)(=O)=O)=C1OC ULZJFSDAGGMEOD-UHFFFAOYSA-N 0.000 description 2
- WCWSAJZHQFNXJB-UHFFFAOYSA-N CCCCNC(NS(CC1CCCCC1)(=O)=O)=O Chemical compound CCCCNC(NS(CC1CCCCC1)(=O)=O)=O WCWSAJZHQFNXJB-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZEJWPORAGQSKFA-UHFFFAOYSA-N O=C(NCC1CCCCC1)NS(C1CCCCC1)(=O)=O Chemical compound O=C(NCC1CCCCC1)NS(C1CCCCC1)(=O)=O ZEJWPORAGQSKFA-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 1
- LVVLYDLSCDLQMG-UHFFFAOYSA-N 1,1-bis-(4-methylphenyl)sulfonylurea Chemical class Cc1ccc(cc1)S(=O)(=O)N(C(N)=O)S(=O)(=O)c1ccc(C)cc1 LVVLYDLSCDLQMG-UHFFFAOYSA-N 0.000 description 1
- ZRIXMRNZDNXRIH-UHFFFAOYSA-N 1,3-bis[(2-methylphenyl)sulfonyl]urea Chemical compound Cc1ccccc1S(=O)(=O)NC(=O)NS(=O)(=O)c1ccccc1C ZRIXMRNZDNXRIH-UHFFFAOYSA-N 0.000 description 1
- RCVYTGONPBOXIF-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)sulfonyl-3-(2-methylpropyl)urea Chemical compound CC1=C(C=C(C=C1)S(=O)(=O)NC(=O)NCC(C)C)Cl RCVYTGONPBOXIF-UHFFFAOYSA-N 0.000 description 1
- JTDKEDJPCUTMJL-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JTDKEDJPCUTMJL-UHFFFAOYSA-N 0.000 description 1
- VJLQCOHTKNASNE-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 VJLQCOHTKNASNE-UHFFFAOYSA-N 0.000 description 1
- DNIIWANRGRGVRG-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-cyclohexylurea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 DNIIWANRGRGVRG-UHFFFAOYSA-N 0.000 description 1
- URMFMMLIAIRVRO-UHFFFAOYSA-N 1-butyl-3-(2-methylphenyl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1C URMFMMLIAIRVRO-UHFFFAOYSA-N 0.000 description 1
- ZTXKBNXYCAWZFY-UHFFFAOYSA-N 1-butyl-3-(3-chloro-4-methylphenyl)sulfonylurea Chemical compound CC1=C(C=C(C=C1)S(=O)(=O)NC(=O)NCCCC)Cl ZTXKBNXYCAWZFY-UHFFFAOYSA-N 0.000 description 1
- IGHUGYISOXSCRI-UHFFFAOYSA-N 1-butyl-3-naphthalen-2-ylsulfonylurea Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)NC(=O)NCCCC IGHUGYISOXSCRI-UHFFFAOYSA-N 0.000 description 1
- NGCONVFTEJQTHZ-UHFFFAOYSA-N 1-cyclohexylsulfonyl-3-(2-methylpropyl)urea Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)NCC(C)C NGCONVFTEJQTHZ-UHFFFAOYSA-N 0.000 description 1
- SHVCKTUQDUTJDT-UHFFFAOYSA-N 1-cyclopentyl-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCC1 SHVCKTUQDUTJDT-UHFFFAOYSA-N 0.000 description 1
- TYRVXLIAZXPCND-UHFFFAOYSA-N 1-ethyl-3-(4-methylphenyl)sulfonylurea Chemical compound CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 TYRVXLIAZXPCND-UHFFFAOYSA-N 0.000 description 1
- WSYHGPCRWCSNOC-UHFFFAOYSA-N 1-heptyl-3-(4-methylphenyl)sulfonylurea Chemical compound CCCCCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 WSYHGPCRWCSNOC-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- MUTDXQJNNJYAEG-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(dimethylamino)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)N(C)C MUTDXQJNNJYAEG-UHFFFAOYSA-N 0.000 description 1
- HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZLWBVTOHKZXGIU-UHFFFAOYSA-N C(C1=CC=CC=C1)S(=O)(=O)NC(=O)NS(=O)(=O)CC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)S(=O)(=O)NC(=O)NS(=O)(=O)CC1=CC=CC=C1 ZLWBVTOHKZXGIU-UHFFFAOYSA-N 0.000 description 1
- AZILYAJHYBTQJL-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)S(=O)(=O)NC(=O)NC1CCCCC1 Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)NC(=O)NC1CCCCC1 AZILYAJHYBTQJL-UHFFFAOYSA-N 0.000 description 1
- LXLUTMFWSPJANZ-UHFFFAOYSA-N C1=C(C=CC=2CCCCC1=2)S(=O)(=O)NC(=O)NCC(C)C Chemical compound C1=C(C=CC=2CCCCC1=2)S(=O)(=O)NC(=O)NCC(C)C LXLUTMFWSPJANZ-UHFFFAOYSA-N 0.000 description 1
- CKFHAFLKWXJTOL-UHFFFAOYSA-N CC(C)C(C=C1)=CC=C1S(NC(NS(C1=CC=C(C(C)C)C=C1)(=O)=O)=O)(=O)=O Chemical compound CC(C)C(C=C1)=CC=C1S(NC(NS(C1=CC=C(C(C)C)C=C1)(=O)=O)=O)(=O)=O CKFHAFLKWXJTOL-UHFFFAOYSA-N 0.000 description 1
- CAJMLLBVHHHGGS-UHFFFAOYSA-N CCCCCCNC(NS(C1CCCCC1)(=O)=O)=O Chemical compound CCCCCCNC(NS(C1CCCCC1)(=O)=O)=O CAJMLLBVHHHGGS-UHFFFAOYSA-N 0.000 description 1
- GKKQDMAZFBKRLQ-UHFFFAOYSA-N CCCCS(NC(NS(CCCC)(=O)=O)=O)(=O)=O Chemical compound CCCCS(NC(NS(CCCC)(=O)=O)=O)(=O)=O GKKQDMAZFBKRLQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical class CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- IIZVFUFUALIPHV-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NCC(C)C Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NCC(C)C IIZVFUFUALIPHV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- OPOKQGZVULEBEJ-UHFFFAOYSA-N [Na].NS(N)(=O)=O Chemical compound [Na].NS(N)(=O)=O OPOKQGZVULEBEJ-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QOCVOOWVZVIZEO-UHFFFAOYSA-N benzene;sulfamide Chemical class NS(N)(=O)=O.C1=CC=CC=C1 QOCVOOWVZVIZEO-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical class NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BNEBFAXBFRAIGF-UHFFFAOYSA-N ethyl N-acetamido-N-(benzenesulfonyl)carbamate Chemical compound C(C)OC(N(S(=O)(=O)C1=CC=CC=C1)NC(C)=O)=O BNEBFAXBFRAIGF-UHFFFAOYSA-N 0.000 description 1
- XSXLCQLOFRENHC-UHFFFAOYSA-N ethyl n-benzylcarbamate Chemical compound CCOC(=O)NCC1=CC=CC=C1 XSXLCQLOFRENHC-UHFFFAOYSA-N 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- XWQXWXZSAIORQC-UHFFFAOYSA-N methyl N-(3,4-dimethylphenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC(=C(C=C1)C)C)=O XWQXWXZSAIORQC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QHSZICITQBPJNK-UHFFFAOYSA-N methyl n-(benzenesulfonyl)carbamate Chemical compound COC(=O)NS(=O)(=O)C1=CC=CC=C1 QHSZICITQBPJNK-UHFFFAOYSA-N 0.000 description 1
- CDQYMWJDKABVFK-UHFFFAOYSA-N n-(oxomethylidene)cyclohexanesulfonamide Chemical compound O=C=NS(=O)(=O)C1CCCCC1 CDQYMWJDKABVFK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20751A DE1043318B (de) | 1956-07-10 | 1956-07-10 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH351589A true CH351589A (de) | 1961-01-31 |
Family
ID=7089800
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH351589D CH351589A (de) | 1956-07-10 | 1957-01-07 | Verfahren zur Herstellung von Sulfonylharnstoffen |
| CH351588D CH351588A (de) | 1956-07-10 | 1957-01-07 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH351588D CH351588A (de) | 1956-07-10 | 1957-01-07 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT195436B (da) |
| CH (2) | CH351589A (da) |
| DE (1) | DE1043318B (da) |
| DK (1) | DK89984C (da) |
| FR (1) | FR1172148A (da) |
-
1956
- 1956-07-10 DE DEF20751A patent/DE1043318B/de active Pending
- 1956-12-15 AT AT195436D patent/AT195436B/de active
-
1957
- 1957-01-07 CH CH351589D patent/CH351589A/de unknown
- 1957-01-07 CH CH351588D patent/CH351588A/de unknown
- 1957-01-26 DK DK32057A patent/DK89984C/da active
- 1957-01-29 FR FR1172148D patent/FR1172148A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH351588A (de) | 1961-01-31 |
| AT195436B (de) | 1958-02-10 |
| FR1172148A (fr) | 1959-02-05 |
| DE1043318B (de) | 1958-11-13 |
| DK89984C (da) | 1960-11-14 |
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