Diethanolamine → 4-Amino-N,N-bis(2-hydroxyethyl)benzenesulfonamide

Participants

Reaction Steps

N1,N1 -bis(2-hydroxyethyl) sulfanilamide was prepared as follows. (This method was taken in part from G. DiModica and E. Angeletti, Gazz. chim. ital., 1960, 90, 434-9 [CA 55:11344d].) A mixture of sodium carbonate (55.6 g), D.I. water (120 mL), and diethanolamine (57.8 g) was stirred and heated to 60°-70° C. Acetylsulfanilyl chloride (116.8 g) was added as a solid over an hour. D.I. water (225 mL) was added in portions during the acetylsulfanilyl chloride addition to keep the mixture stirrable. The mixture was stirred for an additional 3 hours at 60°-70° C., then allowed to cool to room temperature for about 16 hours. The solids were isolated by filtration and washed with 200 mL cold D.I. water.

Provenance & Evidence