Chloroacetanilide → 4-(2-Chloroacetamido)benzene-1-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

Chloroacetanilide (4.53 g) is slowly added to chlorosulfonic acid (7.5 mL) at a temperature of 5° C. The solution is heated to 65° C. and thionyl chloride (0.78 mL) is added. After 10 minutes of gas evolution the reaction was cooled to room temperature. The mixture is added to ice/water (2.14 g/3.2 mL) and stirred for 30 minutes. The product was filtered, washed with water (60 mL), placed under vacuum at 50° C. and dried to a constant weight. The product is a white powder, yield: 4.81 g (67%).

Provenance & Evidence