Hydrochloric Acid → 4-[(Dimethylsulfamoyl)amino]-N-phenylbenzamide

Reaction equation

[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:17][N:18]([CH3:23])[S:19](Cl)(=[O:21])=[O:20].Cl>N1C=CC=CC=1>[CH3:17][N:18]([CH3:23])[S:19]([NH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1)(=[O:21])=[O:20]

Participants

Procedure

To a solution of 1.0 g of 4-aminobenzanilide 4 dissolved in 10 ml of dried pyridine is added 1.01 g of dimethylaminosulfonyl chloride 5 at room temperature, and the mixture is stirred over-night. The reaction mixture is poured into ice-water, acidified with 6N hydrochloric acid, and extracted with a mixture of methylene chloride-methanol. The organic layer is extracted again with 10% sodium hydroxide solution. The alkaline layer is acidified with 6N hydrochloric acid; the precipitate is collected by filtration and recrystallized from methanol to give 864 mg of 4-[(dimethylaminosulfonyl)amino]benzanilide 6 as crystals, m.p. 213°-215° C.