Benzocaine → HCID 13503404, compound

Participants

Reaction Steps

To a stirred solution of 23.55 g. of bis(p-chlorophenyl)acetic acid in 250 ml. of benzene is added dropwise 33.1 g. of sulfonyl chloride. The mixture is refluxed 5 hours, the solvent is evaporated, and the residue is evaporated from three 250 ml. portions of benzene, giving 26.06 g. of bis(p-chlorophenyl)acetyl chloride as an oil. To this oil is added a solution of 27.7 g. of benzocaine. The mixture is stirred overnight, filtered, washed with 200 ml. each of 10% hydrochloric acid, saturated sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, and evaporated. The residue is crystallized twice from 200 ml. of ethanol, giving 25.76 g. of the desired product as colorless needles, m.p. 171°-172° C.

Provenance & Evidence