BE442759A - - Google Patents

Info

Publication number

BE442759A

BE442759A BE442759DA BE442759A BE 442759 A BE442759 A BE 442759A BE 442759D A BE442759D A BE 442759DA BE 442759 A BE442759 A BE 442759A

Authority

BE

Belgium

Prior art keywords

group

acid

compounds

amino

nitro

Prior art date

Links

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• 239000002253 acid Substances 0.000 claims description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
• 150000001875 compounds Chemical class 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 229910006069 SO3H Inorganic materials 0.000 claims description 4
• 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 3
• 239000011230 binding agent Substances 0.000 claims description 3
• 238000000034 method Methods 0.000 claims description 3
• 229940124530 sulfonamide Drugs 0.000 claims description 3
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 150000003839 salts Chemical class 0.000 claims description 2
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
• 150000003456 sulfonamides Chemical class 0.000 claims description 2
• 150000003460 sulfonic acids Chemical class 0.000 claims description 2
• 150000001299 aldehydes Chemical class 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 238000009835 boiling Methods 0.000 description 6
• 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 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 238000001816 cooling Methods 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000003610 charcoal Substances 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
• HTZGWONWPJNYOM-UHFFFAOYSA-N [(4-aminophenyl)sulfonylamino]methanesulfonic acid Chemical compound NC1=CC=C(S(=O)(=O)NCS(O)(=O)=O)C=C1 HTZGWONWPJNYOM-UHFFFAOYSA-N 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• 125000002252 acyl group Chemical group 0.000 description 2
• OBESRABRARNZJB-UHFFFAOYSA-N aminomethanesulfonic acid Chemical compound NCS(O)(=O)=O OBESRABRARNZJB-UHFFFAOYSA-N 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 239000007859 condensation product Substances 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
• UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
• BZBRJSZSFBIWAU-UHFFFAOYSA-N NC1=CC=C(C=C1)S(=O)(=O)C(S(=O)(=O)O)N Chemical compound NC1=CC=C(C=C1)S(=O)(=O)C(S(=O)(=O)O)N BZBRJSZSFBIWAU-UHFFFAOYSA-N 0.000 description 1
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
• 125000003282 alkyl amino group Chemical group 0.000 description 1
• 150000008331 benzenesulfonamides Chemical class 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 230000000249 desinfective effect Effects 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 239000013067 intermediate product Substances 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
• 239000000203 mixture Substances 0.000 description 1
• KERKSHQWMCWPBT-UHFFFAOYSA-N n-phenylacetamide;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.CC(=O)NC1=CC=CC=C1 KERKSHQWMCWPBT-UHFFFAOYSA-N 0.000 description 1
• 150000002828 nitro derivatives Chemical class 0.000 description 1
• HKTBRYQNVRPBCF-UHFFFAOYSA-N nitrobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 HKTBRYQNVRPBCF-UHFFFAOYSA-N 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
• 125000000565 sulfonamide group Chemical group 0.000 description 1