BE497247A - - Google Patents

Info

Publication number

BE497247A

BE497247A BE497247DA BE497247A BE 497247 A BE497247 A BE 497247A BE 497247D A BE497247D A BE 497247DA BE 497247 A BE497247 A BE 497247A

Authority

BE

Belgium

Prior art keywords

group

thiodiazol

benzene

aminogenic

transformed

Prior art date

Links

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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
• 238000000034 method Methods 0.000 claims description 9
• 150000001875 compounds Chemical class 0.000 claims description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
• 230000001034 aminogenic effect Effects 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 5
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
• -1 fatty acid halide Chemical class 0.000 claims description 4
• ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 4
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
• 239000012346 acetyl chloride Substances 0.000 claims description 3
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
• 150000001447 alkali salts Chemical class 0.000 claims description 2
• 150000004820 halides Chemical class 0.000 claims description 2
• 238000002844 melting Methods 0.000 claims description 2
• 230000008018 melting Effects 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 239000000194 fatty acid Substances 0.000 claims 2
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims 2
• ODEKRQRHPSDSTI-UHFFFAOYSA-N C(C)(=O)N(NC(=S)N)S(=O)(C1=CC=C(C=C1)N)=O Chemical compound C(C)(=O)N(NC(=S)N)S(=O)(C1=CC=C(C=C1)N)=O ODEKRQRHPSDSTI-UHFFFAOYSA-N 0.000 claims 1
• 235000014113 dietary fatty acids Nutrition 0.000 claims 1
• 229930195729 fatty acid Natural products 0.000 claims 1
• 230000007062 hydrolysis Effects 0.000 claims 1
• 238000006460 hydrolysis reaction Methods 0.000 claims 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
• 230000001131 transforming effect Effects 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 239000000243 solution Substances 0.000 description 3
• OSZFJGLXXUAMEJ-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonyl chloride Chemical compound CC(=O)C1=CC(N)=CC=C1S(Cl)(=O)=O OSZFJGLXXUAMEJ-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
• 230000021736 acetylation Effects 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 230000003385 bacteriostatic effect Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• LJWKFGGDMBPPAZ-UHFFFAOYSA-N ethoxyethane;toluene Chemical compound CCOCC.CC1=CC=CC=C1 LJWKFGGDMBPPAZ-UHFFFAOYSA-N 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 239000012493 hydrazine sulfate Substances 0.000 description 1
• 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000005416 organic matter Substances 0.000 description 1
• 244000052769 pathogen Species 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1