Hydrochloric Acid → 2-Amino-4-(phenylthio)phenol hydrochloride

Participants

Reaction Steps

A solution of 5-(phenylthio)benzo[d]oxazole (1.04 g, 4.6 mmol) and conc. HCl (0.97 mL, 11 mmol) under nitrogen in 4.6 mL EtOH in a 50 mL rbf fitted with a water-cooled reflux condensor was placed in a 100° C. bath. After 2 h, the mixture was cooled, concentrated in vacuo and dried to give a yellow solid. The material was sonicated in 10 mL DCM, filtered, rinsing with DCM, and dried to give 2-amino-4-(phenylthio)phenol hydrochloride as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.72 (s, 1H), 8.75 (br. s., 1H), 7.28-7.35 (m, 2H), 7.12-7.25 (m, 5H), 6.99 (d, J=8.0 Hz, 1H), 4.32 (br. s., 2H).

Provenance & Evidence