Synthesis of N-acetylsulfanilyl chloride (p-acetamidobenzenesulfonyl chloride)

Preparation of N-acetylsulfanilyl chloride

Preparation of N-acetylsulfanilyl chloride (p-acetamidobenzenesulfonyl chloride)

Preparation of N-acetylsulfanilyl chloride (p-acetamidobenzenesulfonyl chloride)

25 g of dry powdered acetanilide are added with occasional stirring, to 63 ml (or 110 g) of chlorosulfonic acid and the mixture is heated to 60-70° C for 2 hours. Then the reaction mixture is cooled to room temperature and poured carefully on to about 500 g of crushed ice. The crude N-acetylsulfanilyl chloride separates as a white solid, which is filtered, washed it thoroughly with water in order to remove inorganic acids. This crude N-acetylsulfanilyl chloride is sufficiently pure for most synthesis. However, to obtain pure N-acetylsulfanilyl chloride, crystallization from chloroform yields 38 g of colorless crystals, which melt at 149-150° C.

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

IUPAC Name

4-acetamidobenzenesulfonyl chloride

InChI

InChI=1S/C8H8ClNO3S/c1-6(11)10-7-2-4-8(5-3-7)14(9,12)13/h2-5H,1H3,(H,10,11)

InChI Key

GRDXCFKBQWDAJH-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

4-AAB-SC cpd, 4-acetamidobenzene sulfonyl chloride

Depositor-Supplied Synonyms

N-Acetylsulfanilyl chloride, 121-60-8, 4-Acetamidobenzenesulfonyl chloride, 4-Acetamidobenzene-1-Sulfonyl Chloride, Dagenan chloride, 4-Acetamidophenylsulfonyl chloride, 4-(ACETYLAMINO)BENZENESULFONYL CHLORIDE, Benzenesulfonyl chloride, 4-(acetylamino)-, p-Acetamidobenzenesulfonyl chloride, Acetylsulfanilyl chloride, p-Acetaminobenzenesulfonyl chloride, N4-Acetylsulfanilyl chloride, Acetanilide-p-sulfonyl chloride, Sulfanilyl chloride, N-acetyl-, p-Acetylaminobenzenesulfochloride, p-Acetamidophenylsulfonyl chloride, 4-Chlorosulfonylacetanilide, N-Acetylsulphanilyl chloride, p-(Chlorosulfonyl)acetanilide, UNII-LIX4M9AIVM, NSC 127860, 4′-(Chlorosulfonyl)acetanilide, HSDB 2712, GRDXCFKBQWDAJH-UHFFFAOYSA-N, N(sup 4)-Acetylsulfanilyl chloride, EINECS 204-485-1, p-Acetylaminobenzenesulfonyl chloride, 4-Acetylamino-benzenesulfonyl chloride, p-Acetyl aminobenzene sulfonyl chloride, Benzenesulfonic acid, 4-acetamido-, chloride, Sulfanilyl chloride, N-acetyl- (6CI,7CI,8CI), N-[4-(chlorosulfonyl)phenyl]acetamide, ACMC-209aeo, LIX4M9AIVM, N-Acetylsulfanilylchloride, DSSTox_CID_6981, AC1Q1KU0, AC1Q6YM2, DSSTox_RID_78273, N-Acetyl sulfanilyl chloride, DSSTox_GSID_26981, SCHEMBL58191, N-acetyl sulphanilyl chloride, KSC174S4L, 4-N-acetylsulphanilyl chloride, 112747_ALDRICH, AC1L1R37, CCRIS 8936, CHEMBL3185390, 4-acetamidobenzenesulfonylchloride, CTK0H4945, p-acetamidobenzenesulphonylchloride, MolPort-001-768-953, 4-acetaminobenzenesulfonyl chloride, BB_SC-5612, 4-acetamidophenyl sulfonyl chloride, 4-acetamidobenzenesulphonyl chloride, 4-acetamino-benzenesulfonyl chloride, 4-acetylaminophenylsulfonyl-chloride, p-Acetamidobenzene sulfonyl chloride, 4-Acetamidobenzene sulfonyl chloride, 4-Acetaminobenzene sulfonyl chloride, 4-Acetylaminobenzenesulfonyl chloride, 4-Acetylaminobenzenesulphonylchloride, p-acetaminobenzene sulphonyl chloride, Tox21_202556, 4-acetamido-benzenesulphonyl chloride, ANW-17758, AR-1G0331, BBL010089, NSC127860, SBB058755, STK358538, 4(acetylamino)benzenesulfonyl chloride, 4-acetylaminobenzene sulfonyl chloride, AKOS000119788, MCULE-3025114875, NE10490, NSC-127860, RP28084, RP28087, 4-acetamid obenzene-1-sulfonyl chloride, 4-(acetylamino)benzene sulfonyl chloride, NCGC00260105-01, AK134881, AN-22851, BP-22022, CAS-121-60-8, LS-32135, AB1002988, DB-002824, KB-188807, RT-001470, ST2405498, A0074, FT-0082825, FT-0617377, FT-0661175, ST51037895, 4-(ACETYLAMINO)-BENZENESULFONYL CHLORIDE, I01-0477, 3B3-034532, F0808-2025, InChI=1/C8H8ClNO3S/c1-6(11)10-7-2-4-8(5-3-7)14(9,12)13/h2-5H,1H3,(H,10,11

Removed Synonyms

CID8481, ASC, 1231-74-9

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