Benzyl Bromide → 3-Benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid

Participants

Reaction Steps

A mixture of 3-amino-4-isopropylamino-5-sulphamyl-benzoic acid (2.62 g), benzyl bromide (4.28 g), and anhydrous ethanol (25 ml) was refluxed for 24 hours. The reaction mixture was evaporated in vacuo. 1N sodium hydroxide (30 ml) was added, and the mixture was heated on a steam bath for 1 hour. After cooling and extracting with diethyl ether, the aqueous layer was adjusted to a pH of 3 by addition of 4N hydrochloric acid. The precipitated 3-benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid was collected by suction and recrystallized from aqueous ethanol. The melting point was 233°-234°C.

Provenance & Evidence