Sodium Hydroxide → 2-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid

Participants

Reaction Steps

To a water (20 mL) solution of 2-hydrazino-benzoic acid hydrochloride (2.508 g, 13.30 mmol) was added water solution of sodium hydroxide (1.029 N, d=1.040, 26.81 g, 26.60 mmol) followed by bis(carboxymethyl)trithiocarbonate (3.006 g, 13.28 mmol). The mixture was stirred at reflux temperature for 10 h, cooled to room temperature and stirred for 50 h. The solid product was filtered off and washed on funnel successively with water (2×10 ml), ether (5 mL) and hexane (20 mL). The material was dried in a vacuum oven at 80° C. for 5 h to afford 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (2.93 g, 82%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 4.33 (1H, bs), 6.66 (1H, m), 6.90 (1H, m), 7.40 (1H, m), 7.89 (1H, m), 13.37 (1H, bs). ESI-MS: 267.0.

Provenance & Evidence