Synthesis of 4-acetamidobenzenesulfonamide

Preparation of 4-acetamidobenzenesulfonamide (N-(4-sulfamoylphenyl)acetamide; acetylsulfanilamide)

Preparation of 4-acetamidobenzenesulfonamide (N-(4-sulfamoylphenyl)acetamide; acetylsulfanilamide)

Preparation of 4-acetamidobenzenesulfonamide (N-(4-sulfamoylphenyl)acetamide; acetylsulfanilamide)

39 g of N-acetylsulfanilyl chloride cautiously mixed with 120 ml of concentrated ammonia solution (d=0.880). A vigorous reaction with the evolution of heat takes place and the mixture is stirred until a smooth thin paste is obtained. This paste is heated at 70° C for 30 minutes with occasional stirring and after cooling the mixture is neutralized with dilute sulfuric acid. The solution is filtered, 4-acetamidobenzenesulfonamide washed with cold water and dried. Crude 4-acetamidobenzenesulfonamide is sufficiently pure for most synthesis. However, to obtain the pure product, 4-acetamidobenzenesulfonamide is crystallized from hot water yielding colorless crystals, which melt at 219° C.

Practical organic chemistry, by F. G. Mann, 181, 1960

IUPAC Name

N-(4-sulfamoylphenyl)acetamide

InChI

InChI=1S/C8H10N2O3S/c1-6(11)10-7-2-4-8(5-3-7)14(9,12)13/h2-5H,1H3,(H,10,11)(H2,9,12,13)

InChI Key

PKOFBDHYTMYVGJ-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC1=CC=C(C=C1)S(=O)(=O)N

MeSH Synonyms

Acetopt, Acetylsulfanilamide, AK Sulf, AK-Sulf, Akorn Brand of Sulfacetamide Sodium, Albucid, Alcon Brand 1 of Sulfacetamide Sodium, Alcon Brand 2 of Sulfacetamide Sodium, Allergan Brand of Sulfacetamide Sodium, Antébor, Belph 10, Belph-10, Bleph, Ceta Sulfa, Cetamide, Cetamide, Isopto, Chauvin Brand of Sulfacetamide Sodium, Colircusi Sulfacetamida, Coliriocilina Sulfacetam, Grin Brand of Sulfacetamide Sodium, Isopto Cetamide, Médix Brand of Sulfacetamide Sodium, Medical Brand of Sulfacetamide Sodium, Monosodium Salt, Sulfacetamide, Novartis Brand of Sulfacetamide Sodium, Pharmafair Brand of Sulfacetamide Sodium, Schering Brand of Sulfacetamide Sodium, Sigma Brand of Sulfacetamide Sodium, Sodium Sulamyd, Sodium, Sulfacetamide, Sulamyd, Sodium, Sulf 10, Sulf-10, Sulfacetam, Coliriocilina, Sulfacetamida, Colircusi, Sulfacetamide, Sulfacetamide Monosodium Salt, Sulfacetamide Sodium, Sulfacetamide, Monosodium Salt, Anhydrous, Sulfacil, Sulfacyl, Sulfair, Sulphacetamide

Depositor-Supplied Synonyms

4-Acetamidobenzenesulfonamide, N-(4-Sulfamoylphenyl)acetamide, 121-61-9, Acetylsulfanilamide, Neotherapol, Erytrin, p-Sulfamylacetanilide, N4-Acetsulfanilamide, p-Acetamidobenzenesulfonamide, N4-ACETYLSULFANILAMIDE, 4′-Sulfamoylacetanilide, 4-Acetylaminobenzenesulfonamide, Sulfanilamide-N4-acetate, Acetanilide, 4′-sulfamoyl-, p-Sulfamoylacetanilide, 4′-Sulfamylacetanilide, N’-Acetylsulphanilamide, 4′-Sulphamoylacetanilide, Benzenesulfonamide, p-acetamido-, N-(4-Sulphamoylphenyl)acetamide, p-(Acetylamino)benzenesulfonamide, Acetsulphanilamide, Benzenesulfonamide, 4-(acetylamino)-, NSC 217, N-4-Acetylsulfanilamide, A-319, N(sup 4)-Acetsulfanilamide, N(sup 4)-Acetylsulfanilamide, Acetamide, N-[4-(aminosulfonyl)phenyl]-, N-(4-Sulfamylphenyl)acetamide, CCRIS 6813, Sulfanilamide-N(sup 4)-acetate, N-(4-Sulfamoyl-phenyl)-acetamide, PKOFBDHYTMYVGJ-UHFFFAOYSA-N, EINECS 204-486-7, SBB016985, N-(4-(Aminosulfonyl)phenyl)acetamide, N-[4-(Aminosulfonyl)phenyl]acetamide, N-[4-(aminosulfonyl)phenyl]-Acetamide, BRN 0746675, Acetamide, N-(4-(aminosulfonyl)phenyl)-, AI3-08023, PubChem13328, N4 -acetylsulfanilamide, ACMC-209aeq, Enamine_001217, CHEMBL687, AC1L1R3A, DSSTox_CID_21529, DSSTox_RID_79768, N4-ACETYL METABOLITE, DSSTox_GSID_41529, Oprea1_094374, Oprea1_582774, SCHEMBL359721, 4-Acetylaminobenzenesulphonamide, aromatic sulfonamide compound 8, NSC217, 4-N-Acetylaminophenylsulfonamide, UNII-340484WZ3L, CTK4B2552, PKOFBDHYTMYVGJ-UHFFFAOYSA-, NSC-217, MolPort-000-516-339, HMS1397H07, Tox21_300850, ANW-17760, DNC005748, NSC406839, STL308440, ZINC00134036, AKOS000141336, 340484WZ3L, MCULE-8661643137, NSC-406839, PS-4449, SDCCGMLS-0064665.P001, Acetamide,N-[4-(aminosulfonyl)phenyl]-, N-[4-(Aminosulfonyl)phenyl]acetamide #, NCGC00248191-01, NCGC00254753-01, AJ-12210, AK-41303, AN-25645, CAS-121-61-9, KB-36116, LS-10827, SC-57988, DB-061940, TC-106505, A0115, FT-0647475, ST50168205, A18135, K-1622, Acetamide, N-(4-(aminosulfonyl)phenyl)- (9CI), I01-10155, T0516-5952, InChI=1/C8H10N2O3S/c1-6(11)10-7-2-4-8(5-3-7)14(9,12)13/h2-5H,1H3,(H,10,11)(H2,9,12,13)

Removed Synonyms

C8H10N2O3S, CID8482, 4-14-00-02704 (Beilstein Handbook Reference)

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