Water → 2-Chloro-6-phenylbenzenesulfonamide

Participants

Reaction Steps

A solution of 2-chloro-N-(1,1-dimethylethyl)-6-phenylbenzenesulfonamide (23 g, 0.071 mol) in a mixture of 120 ml trifluoroacetic acid (TFA) plus 4 ml water was heated to reflux for 2 hours. The TFA was evaporated in vacuo and the residue partitioned between methylene chloride and water. The organic layer was dried (MgSO4), evaporated, and the residue crystallized from ether/methylene chloride to afford 15.9 g of crystalline solid in two crops, m.p. 185°-87°. NMR (90 MHZ, CDCl3) 6.45 (s, br, NH2). 7.3-7.7 (m, 8H) ppm.

Provenance & Evidence