Water → 7-Chloro-1H-pyrido[2,3-b][1,4]thiazin-2(3H)-one

Participants

Reaction Steps

To a stirred solution of ethyl 2-mercaptoacetate (2.0 mL, 18.4 mmol) in water (5.03 mL, 12.27 mmol) was added NaOH (0.491 g, 12.27 mmol). The reaction was stirred at rt for 10 min. After this time a solution of 2,5-dichloropyridin-3-amine (2.0 g, 12.27 mmol) in EtOH (20 mL) was added and the reaction was heated at reflux for 4 days and cooled to rt. The resulting precipitate was filtered and washed with hexanes (50 mL) and MeOH (5 mL) to give 7-chloro-1H-pyrido-[2,3-b][1,4]thiazin-2(3H)-one as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.76 (1H, d, J=0.6 Hz), 8.15 (1H, d, J=2.2 Hz), 7.31 (1H, d, J=2.3 Hz), 3.59-3.74 (2H, m). Mass Spectrum (ESI) m/e=201.0 (M+1).

Provenance & Evidence