BE446582A - - Google Patents

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Publication number

BE446582A

BE446582A BE446582DA BE446582A BE 446582 A BE446582 A BE 446582A BE 446582D A BE446582D A BE 446582DA BE 446582 A BE446582 A BE 446582A

Authority

BE

Belgium

Prior art keywords

grams

water

hydrochloric acid

mol

alcohol

Prior art date

Links

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• -1 aromatic sulfonamides Chemical class 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
• 108020001305 NR1 subfamily Proteins 0.000 claims 1
• 230000007062 hydrolysis Effects 0.000 claims 1
• 238000006460 hydrolysis reaction Methods 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 101150009274 nhr-1 gene Proteins 0.000 claims 1
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 239000000243 solution Substances 0.000 description 11
• 238000006243 chemical reaction Methods 0.000 description 10
• 150000001875 compounds Chemical class 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 235000011181 potassium carbonates Nutrition 0.000 description 8
• 239000000047 product Substances 0.000 description 7
• 238000003756 stirring Methods 0.000 description 6
• 235000011118 potassium hydroxide Nutrition 0.000 description 5
• 235000011121 sodium hydroxide Nutrition 0.000 description 5
• 125000004442 acylamino group Chemical group 0.000 description 4
• 230000007935 neutral effect Effects 0.000 description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
• 238000007127 saponification reaction Methods 0.000 description 4
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 238000002425 crystallisation Methods 0.000 description 3
• 230000008025 crystallization Effects 0.000 description 3
• AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 3
• 239000012530 fluid Substances 0.000 description 3
• PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000002349 favourable effect Effects 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000003472 neutralizing effect Effects 0.000 description 2
• 235000015320 potassium carbonate Nutrition 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 150000003839 salts Chemical class 0.000 description 2
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• GNDKYAWHEKZHPJ-UHFFFAOYSA-N 2-nitrobenzenesulfonimidic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O GNDKYAWHEKZHPJ-UHFFFAOYSA-N 0.000 description 1
• 208000035143 Bacterial infection Diseases 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• RJXZKCBLNZNCEQ-UHFFFAOYSA-N C(C)(=O)N(C(=O)OCC)CS(=O)(C1=CC=C(C=C1)N)=O Chemical compound C(C)(=O)N(C(=O)OCC)CS(=O)(C1=CC=C(C=C1)N)=O RJXZKCBLNZNCEQ-UHFFFAOYSA-N 0.000 description 1
• QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 description 1
• OLIPUSNWBDOGEO-UHFFFAOYSA-N NC1=CC=C(C=C1)S(=O)(=O)CCNC(=O)OCC Chemical compound NC1=CC=C(C=C1)S(=O)(=O)CCNC(=O)OCC OLIPUSNWBDOGEO-UHFFFAOYSA-N 0.000 description 1
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 230000001476 alcoholic effect Effects 0.000 description 1
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 150000001447 alkali salts Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
• 208000022362 bacterial infectious disease Diseases 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
• 239000003795 chemical substances by application Substances 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 229950004297 lauril Drugs 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000004904 shortening Methods 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 125000001302 tertiary amino group Chemical group 0.000 description 1
• 150000003673 urethanes Chemical class 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1