Acetanilide → N-Acetylsulfanilyl chloride

Participants

Reaction Conditions

Reaction Steps

135.2 g (1.0 mol) of acetanilide are added in portions to 349.5 g (3.0 mol) of chlorosulfonic acid and 2 g of sulfamic acid such that the temperature remains at 40° C. The mixture is then heated to 60° C. and stirred at this temperature for 60 minutes, then 142.8 g (1.2 mol) of thionyl chloride are added dropwise over the course of 2 hours and the mixture is stirred until evolution of gas has ended. For working up, the mixture is dripped into ice water, and the precipitated crystals are filtered off with suction and washed with water. 394.9 g of 4-acetamidobenzenesulfonyl chloride (water content: 41.7%; chloride content: 58.1%), corresponding to 230.2 g (98.5%) calculated as dry material, having a melting point of 139° C. are obtained.

Provenance & Evidence