CH418327A - Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden - Google Patents

Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Info

Publication number: CH418327A
Authority: CH; Switzerland
Prior art keywords: methyl; benzenesulfonyl; semicarbazide; acid amide; methoxy
Prior art date: 1961-10-03

Application number

CH1151862A

Other languages

German (de)

English (en)

Inventor

Aumueller Walter

Weyer Rudi

Weber Helmut

Haack Erich

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1961-10-03

Filing date

1962-10-01

Publication date

1966-08-15

1962-10-01 Application filed by Hoechst Ag filed Critical Hoechst Ag

1966-08-15 Publication of CH418327A publication Critical patent/CH418327A/de

Links

238000000034 method Methods 0.000 title claims description 15
LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
-1 alkoxy radicals Chemical class 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
229910052757 nitrogen Inorganic materials 0.000 description 22
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 12
239000000047 product Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000155 melt Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
229910021529 ammonia Inorganic materials 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
239000008280 blood Substances 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 6
SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 6
239000003610 charcoal Substances 0.000 description 5
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000007858 starting material Substances 0.000 description 5
235000013877 carbamide Nutrition 0.000 description 4
238000001816 cooling Methods 0.000 description 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000002253 acid Substances 0.000 description 3
UGBKOURNNQREPE-UHFFFAOYSA-N azepan-1-amine Chemical compound NN1CCCCCC1 UGBKOURNNQREPE-UHFFFAOYSA-N 0.000 description 3
150000008331 benzenesulfonamides Chemical class 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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 2
IJEDLYZMLJORCY-UHFFFAOYSA-N 3-fluoro-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1F IJEDLYZMLJORCY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZOPSOXNRCGMCEB-UHFFFAOYSA-N COC(NS(=O)(=O)C1=C(C=CC(=C1)Cl)C)=O Chemical compound COC(NS(=O)(=O)C1=C(C=CC(=C1)Cl)C)=O ZOPSOXNRCGMCEB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-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
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
IRPYHGTXYYPKRY-UHFFFAOYSA-N (3,4-dimethylphenyl)sulfonylurea Chemical compound CC=1C=C(C=CC1C)S(=O)(=O)NC(=O)N IRPYHGTXYYPKRY-UHFFFAOYSA-N 0.000 description 1
ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 1
QJARBNAXWFCCKX-UHFFFAOYSA-N 2,3-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(Cl)=C1Cl QJARBNAXWFCCKX-UHFFFAOYSA-N 0.000 description 1
LFEXGBPVZBXATF-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonamide Chemical compound CC1=CC=CC(S(N)(=O)=O)=C1C LFEXGBPVZBXATF-UHFFFAOYSA-N 0.000 description 1
MYOUHONFMXUKQJ-UHFFFAOYSA-N 2,4-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1Cl MYOUHONFMXUKQJ-UHFFFAOYSA-N 0.000 description 1
MGHCDRVTMABICG-UHFFFAOYSA-N 2,4-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C(OC)=C1 MGHCDRVTMABICG-UHFFFAOYSA-N 0.000 description 1
UGBKWMBOBQOCSS-UHFFFAOYSA-N 2,4-dimethylbenzenesulfonimidic acid Chemical compound CC1=CC=C(S(N)(=O)=O)C(C)=C1 UGBKWMBOBQOCSS-UHFFFAOYSA-N 0.000 description 1
INERZUPHFUUUPD-UHFFFAOYSA-N 2,5-dibromobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(Br)=CC=C1Br INERZUPHFUUUPD-UHFFFAOYSA-N 0.000 description 1
UMHSKUILJUFIEK-UHFFFAOYSA-N 2,5-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(Cl)=CC=C1Cl UMHSKUILJUFIEK-UHFFFAOYSA-N 0.000 description 1
MMHMYFWOECSGDR-UHFFFAOYSA-N 2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(N)(=O)=O)=C1 MMHMYFWOECSGDR-UHFFFAOYSA-N 0.000 description 1
STZQAGJQPZCAED-UHFFFAOYSA-N 2,5-dimethylbenzenesulfonamide Chemical compound CC1=CC=C(C)C(S(N)(=O)=O)=C1 STZQAGJQPZCAED-UHFFFAOYSA-N 0.000 description 1
RAJHEZQFXIHNNL-UHFFFAOYSA-N 2,6-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=C(Cl)C=CC=C1Cl RAJHEZQFXIHNNL-UHFFFAOYSA-N 0.000 description 1
NNMFTPMBICNYPF-UHFFFAOYSA-N 2,6-dimethoxybenzenesulfonamide Chemical compound COC1=CC=CC(OC)=C1S(N)(=O)=O NNMFTPMBICNYPF-UHFFFAOYSA-N 0.000 description 1
ZEBMBNNVUIWRIC-UHFFFAOYSA-N 2,6-dimethylbenzenesulfonamide Chemical compound CC1=CC=CC(C)=C1S(N)(=O)=O ZEBMBNNVUIWRIC-UHFFFAOYSA-N 0.000 description 1
UAHWWAIVYPJROV-UHFFFAOYSA-N 2,6-dimethylpiperidin-1-amine Chemical compound CC1CCCC(C)N1N UAHWWAIVYPJROV-UHFFFAOYSA-N 0.000 description 1
QDGORVYVDJZWPF-UHFFFAOYSA-N 2-chloro-5-methylbenzenesulfonamide Chemical compound CC1=CC=C(Cl)C(S(N)(=O)=O)=C1 QDGORVYVDJZWPF-UHFFFAOYSA-N 0.000 description 1
RPYMTSUCKIJOAK-UHFFFAOYSA-N 2-chloro-6-methylbenzenesulfonamide Chemical compound CC1=CC=CC(Cl)=C1S(N)(=O)=O RPYMTSUCKIJOAK-UHFFFAOYSA-N 0.000 description 1
NNBCTZQYASZPPO-UHFFFAOYSA-N 2-methoxy-5-methylbenzenesulfonamide Chemical compound COC1=CC=C(C)C=C1S(N)(=O)=O NNBCTZQYASZPPO-UHFFFAOYSA-N 0.000 description 1
GUBLFDZLZUPTBR-UHFFFAOYSA-N 2-methyl-5-propan-2-ylbenzenesulfonamide Chemical compound CC(C)C1=CC=C(C)C(S(N)(=O)=O)=C1 GUBLFDZLZUPTBR-UHFFFAOYSA-N 0.000 description 1
ILLSOONBCBUBOD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 ILLSOONBCBUBOD-UHFFFAOYSA-N 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
GDXVMOMJBMYCPI-UHFFFAOYSA-N 3,4-dimethyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1C GDXVMOMJBMYCPI-UHFFFAOYSA-N 0.000 description 1
HSPZFYZBTVVAOC-UHFFFAOYSA-N 3,4-dimethylbenzenesulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1C HSPZFYZBTVVAOC-UHFFFAOYSA-N 0.000 description 1
AHNOVNYOUPQVRX-UHFFFAOYSA-N 3,5-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 AHNOVNYOUPQVRX-UHFFFAOYSA-N 0.000 description 1
BRPHYVPAIXLWED-UHFFFAOYSA-N 3,5-dimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(S(N)(=O)=O)=C1 BRPHYVPAIXLWED-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
GZHORVCXHKVLRE-UHFFFAOYSA-N 3-bromo-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1Br GZHORVCXHKVLRE-UHFFFAOYSA-N 0.000 description 1
CFMBNGJNYNLPDL-UHFFFAOYSA-N 3-bromo-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1Br CFMBNGJNYNLPDL-UHFFFAOYSA-N 0.000 description 1
SEBGFUXPGSMUPE-UHFFFAOYSA-N 3-chloro-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1Cl SEBGFUXPGSMUPE-UHFFFAOYSA-N 0.000 description 1
YAUUWNCFVUUNCM-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1Cl YAUUWNCFVUUNCM-UHFFFAOYSA-N 0.000 description 1
JCPWNWBBZNNHDW-UHFFFAOYSA-N 3-fluoro-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1F JCPWNWBBZNNHDW-UHFFFAOYSA-N 0.000 description 1
CDARHVDXDFHNPQ-UHFFFAOYSA-N 3-iodo-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1I CDARHVDXDFHNPQ-UHFFFAOYSA-N 0.000 description 1
PDZOTOVIFNGNPS-UHFFFAOYSA-N 3-methoxy-4-methylbenzenesulfonamide Chemical compound COC1=CC(S(N)(=O)=O)=CC=C1C PDZOTOVIFNGNPS-UHFFFAOYSA-N 0.000 description 1
KQFLTKBUSDMAKA-UHFFFAOYSA-N 4-bromo-3-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Br)C(Cl)=C1 KQFLTKBUSDMAKA-UHFFFAOYSA-N 0.000 description 1
KHVHRFWNCQBULB-UHFFFAOYSA-N 4-chloro-3-methoxybenzenesulfonamide Chemical compound COC1=CC(S(N)(=O)=O)=CC=C1Cl KHVHRFWNCQBULB-UHFFFAOYSA-N 0.000 description 1
MKXKYHVXYMZWIP-UHFFFAOYSA-N 4-chloro-3-methylbenzenesulfonamide Chemical compound CC1=CC(S(N)(=O)=O)=CC=C1Cl MKXKYHVXYMZWIP-UHFFFAOYSA-N 0.000 description 1
JCRJQZODRLHRJV-UHFFFAOYSA-N 4-ethoxy-3-methylbenzenesulfonamide Chemical compound CCOC1=CC=C(S(N)(=O)=O)C=C1C JCRJQZODRLHRJV-UHFFFAOYSA-N 0.000 description 1
DNKWKPATOPAAND-UHFFFAOYSA-N 4-methoxy-2-methylbenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C(C)=C1 DNKWKPATOPAAND-UHFFFAOYSA-N 0.000 description 1
KVVBICXRDBQXOZ-UHFFFAOYSA-N 4-methoxy-3-methylbenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C KVVBICXRDBQXOZ-UHFFFAOYSA-N 0.000 description 1
SGRRWXZGKYYCCC-UHFFFAOYSA-N 5-chloro-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(Cl)C=C1S(N)(=O)=O SGRRWXZGKYYCCC-UHFFFAOYSA-N 0.000 description 1
CBAGDBAYLVYWPM-UHFFFAOYSA-N 5-chloro-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(Cl)C=C1S(N)(=O)=O CBAGDBAYLVYWPM-UHFFFAOYSA-N 0.000 description 1
ZLQUUZQXYILWKO-UHFFFAOYSA-N 5-methoxy-2-methylbenzenesulfonamide Chemical compound COC1=CC=C(C)C(S(N)(=O)=O)=C1 ZLQUUZQXYILWKO-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
SQICEQVNRKRBGM-UHFFFAOYSA-N CC1=C(C=C(C=C1)CCCCCC)S(=O)(=O)N Chemical compound CC1=C(C=C(C=C1)CCCCCC)S(=O)(=O)N SQICEQVNRKRBGM-UHFFFAOYSA-N 0.000 description 1
CTSIWFGEHNIDOW-UHFFFAOYSA-N COC(NS(=O)(=O)C1=CC(=C(C=C1)C)Cl)=O Chemical compound COC(NS(=O)(=O)C1=CC(=C(C=C1)C)Cl)=O CTSIWFGEHNIDOW-UHFFFAOYSA-N 0.000 description 1
RKFXRLPDAZHHOZ-UHFFFAOYSA-N COC(NS(=O)(=O)C1=CC(=C(C=C1)OC)Cl)=O Chemical compound COC(NS(=O)(=O)C1=CC(=C(C=C1)OC)Cl)=O RKFXRLPDAZHHOZ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
244000265913 Crataegus laevigata Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
GGSLXEGVDDGCEY-UHFFFAOYSA-N benzene;sulfuryl diisocyanate Chemical class C1=CC=CC=C1.O=C=NS(=O)(=O)N=C=O GGSLXEGVDDGCEY-UHFFFAOYSA-N 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 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
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
HTHDATSBFYFYTK-UHFFFAOYSA-N hydrazinyloxymethanethioic S-acid Chemical class N(N)OC(O)=S HTHDATSBFYFYTK-UHFFFAOYSA-N 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
QLMOTGNQTSOZNZ-UHFFFAOYSA-N methyl N-(3,4-dimethoxyphenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC(=C(C=C1)OC)OC)=O QLMOTGNQTSOZNZ-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/56—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Hydrogenated Pyridines (AREA)

CH1151862A 1961-10-03 1962-10-01 Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden CH418327A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0035040		1961-10-03

Publications (1)

Publication Number	Publication Date
CH418327A true CH418327A (de)	1966-08-15

Family

ID=7095831

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH1151862A CH418327A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH972166A CH466281A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
CH972066A CH466280A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH972166A CH466281A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
CH972066A CH466280A (de)	1961-10-03	1962-10-01	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden

Country Status (4)

Country	Link
CH (3)	CH418327A (fr)
DK (2)	DK101978C (fr)
FR (1)	FR2837M (fr)
GB (1)	GB979007A (fr)

1962
- 1962-10-01 CH CH1151862A patent/CH418327A/de unknown
- 1962-10-01 CH CH972166A patent/CH466281A/de unknown
- 1962-10-01 CH CH972066A patent/CH466280A/de unknown
- 1962-10-02 DK DK330363AA patent/DK101978C/da active
- 1962-10-02 DK DK330163AA patent/DK102801C/da active
- 1962-10-02 GB GB37347/62A patent/GB979007A/en not_active Expired
1963
- 1963-10-12 FR FR920243A patent/FR2837M/fr active Active

Also Published As

Publication number	Publication date
CH466280A (de)	1968-12-15
CH466281A (de)	1968-12-15
FR2837M (fr)	1964-10-12
GB979007A (en)	1965-01-01
DK102801C (da)	1965-10-11
DK101978C (da)	1965-06-21

Publication	Publication Date	Title
DE2210261C3 (de)	1980-02-28	Verfahren zur Herstellung von 2-Aryl-v-triazolen
CH418327A (de)	1966-08-15	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH440251A (de)	1967-07-31	Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen
DE1545810A1 (de)	1969-12-11	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
AT236401B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT236402B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT234109B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
AT235845B (de)	1964-09-25	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
DE2000339C3 (de)	1979-04-19	Isochinolinderivate
AT236404B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-alkylen-semicarbaziden
CH470356A (de)	1969-03-31	Verfahren zur Herstellung von neuen Sulfamylanthranilsäureamiden
DE1165012B (de)	1964-03-12	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
AT238216B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT234110B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
DE1793111C3 (de)	1976-07-01	Acylaminoäthylbenzolsulfonyl-delta hoch 2-cyclohexenyl-harnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
CH427794A (de)	1967-01-15	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
AT228798B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT234685B (de)	1964-07-10	Verfahren zur Herstellung neuer 3-Phenyl-sydnonimine
AT212312B (de)	1960-12-12	Verfahren zur Herstellung von neuen 2-Sulfonamidothiadiazol-Derivaten
AT235850B (de)	1964-09-25	Verfahren zur Herstellung von neuen Benzolsulfonylalkylensemicarbaziden
AT235848B (de)	1964-09-25	Verfahren zur Herstellung von neuen Benzolsulfonylalkylensemicarbaziden
DE1245380B (de)	1967-07-27	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
AT236412B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT248452B (de)	1966-07-25	Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexylharnstoffen
CH374984A (de)	1964-02-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen