Dichloromethane → 4-(N-methylacetamido)benzene-1-sulfonyl chloride

Reaction equation

[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](=[O:5])[CH3:4].[SH:12]([O:15]Cl)(=O)=[O:13].[Cl:17]CCl>>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([Cl:17])(=[O:15])=[O:13])=[CH:8][CH:7]=1)[C:3](=[O:5])[CH3:4]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 11364N-Methylacetanilide

HCID 178527254HCID 178527254, compound

Product 1

HCID 2931464-(N-methylacetamido)benzene-1-sulfonyl chlorideYield 11%

Procedure

A solution of N-methyl-N-phenylacetamide (11 g, 73.83 mmol) in dichloromethane (20 mL) was added dropwise to HSO3Cl (80 g, 689.66 mmol) at 5° C. The resulting solution was then stirred at room temperature overnight. The reaction mixture was then quenched by adding 100 mL of iced water. The resulting solution was extracted using dichloromethane (2×50 mL) and the organic layers were combined. The residue was purified by column chromatography using a 10:1 ethyl acetate/petroleum ether solvent system to give 2.2 g (11%) of 4-(N-methylacetamido)benzene-1-sulfonyl chloride as a white solid. 1H NMR (CDCl3) δ 8.09 (d, 2H), 7.48 (d, 2H), 3.38 (s, 3H), 2.17 (s, 3H).