CH406192A - Verfahren zur Herstellung von neuen asymmetrisch substituierten Disulfonamiden - Google Patents

Info

Publication number

CH406192A

CH406192A CH218161A CH218161A CH406192A CH 406192 A CH406192 A CH 406192A CH 218161 A CH218161 A CH 218161A CH 218161 A CH218161 A CH 218161A CH 406192 A CH406192 A CH 406192A

Authority

CH

Switzerland

Prior art keywords

methyl

sulfamyl

preparation

asymmetrically substituted

disulfonamides

Prior art date

1960-03-09

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims description 8
• 238000002360 preparation method Methods 0.000 title claims description 3
• -1 alkyl radical Chemical group 0.000 claims description 10
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 8
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
• YSJPYCOLWBGBRG-UHFFFAOYSA-N 2-chloro-3-nitrobenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1Cl YSJPYCOLWBGBRG-UHFFFAOYSA-N 0.000 claims description 4
• 150000001412 amines Chemical class 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• XDPKDZWEXLSCGA-UHFFFAOYSA-N 3-amino-2-chlorobenzenesulfonamide Chemical class NC=1C(=C(C=CC1)S(=O)(=O)N)Cl XDPKDZWEXLSCGA-UHFFFAOYSA-N 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 229910005948 SO2Cl Inorganic materials 0.000 claims description 2
• YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical class [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
• 238000006193 diazotization reaction Methods 0.000 claims description 2
• WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 229960000583 acetic acid Drugs 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 239000012362 glacial acetic acid Substances 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• CADAUKUITLKLMI-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzenesulfonyl chloride Chemical compound NS(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl CADAUKUITLKLMI-UHFFFAOYSA-N 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• YBPHGVBAJQGYDH-UHFFFAOYSA-N n,4-dimethylcyclohexan-1-amine Chemical compound CNC1CCC(C)CC1 YBPHGVBAJQGYDH-UHFFFAOYSA-N 0.000 description 2
• 235000020075 ouzo Nutrition 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 description 2
• 235000011152 sodium sulphate Nutrition 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
• DDRARMBDXDCVRJ-UHFFFAOYSA-N 1-chloro-2-nitrobenzene;sulfurochloridic acid Chemical class OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1Cl DDRARMBDXDCVRJ-UHFFFAOYSA-N 0.000 description 1
• GPRIKJSAAYMDPC-UHFFFAOYSA-N 1-chloro-4-pentylbenzene Chemical compound CCCCCC1=CC=C(Cl)C=C1 GPRIKJSAAYMDPC-UHFFFAOYSA-N 0.000 description 1
• VDNIPNVDBDNDHQ-UHFFFAOYSA-N 2-amino-5-chloro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(Cl)=CC=C1N VDNIPNVDBDNDHQ-UHFFFAOYSA-N 0.000 description 1
• ZAJALNCZCSSGJC-UHFFFAOYSA-N 2-chloro-5-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1Cl ZAJALNCZCSSGJC-UHFFFAOYSA-N 0.000 description 1
• FDDSVQLOFIBCDH-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonamide Chemical compound NC1=CC=C(Cl)C(S(N)(=O)=O)=C1 FDDSVQLOFIBCDH-UHFFFAOYSA-N 0.000 description 1
• 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
• 150000001989 diazonium salts Chemical class 0.000 description 1
• 239000002934 diuretic Substances 0.000 description 1
• 229940030606 diuretics Drugs 0.000 description 1
• 239000002024 ethyl acetate extract Substances 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 230000000630 rising effect Effects 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1