BE438457A - - Google Patents

Info

Publication number

BE438457A

BE438457A BE438457DA BE438457A BE 438457 A BE438457 A BE 438457A BE 438457D A BE438457D A BE 438457DA BE 438457 A BE438457 A BE 438457A

Authority

BE

Belgium

Prior art keywords

sulfanilic acid

reaction

amine

derivative

acetyl

Prior art date

Links

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• HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 229950000244 sulfanilic acid Drugs 0.000 claims description 7
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 5
• -1 acyl sulfanilic acid Chemical compound 0.000 claims description 5
• 229950003476 aminothiazole Drugs 0.000 claims description 5
• 238000006243 chemical reaction Methods 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 150000001875 compounds Chemical class 0.000 claims description 3
• 238000000034 method Methods 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• 239000002904 solvent Substances 0.000 claims description 3
• 150000000565 5-membered heterocyclic compounds Chemical class 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• XCVWCSLKKQOBGY-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonic acid Chemical compound CC(=O)C1=CC(N)=CC=C1S(O)(=O)=O XCVWCSLKKQOBGY-UHFFFAOYSA-N 0.000 claims 1
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000000243 solution Substances 0.000 description 7
• 239000000047 product Substances 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• 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 3
• 239000000203 mixture Substances 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 239000012670 alkaline solution Substances 0.000 description 1
• 235000019441 ethanol Nutrition 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1