2-Acetamido-4-methylthiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide → 2-Amino-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (0.33 g, 1.02 mmol) in 6N hydrochloric acid (4 ml) was heated for 2 h at 80° C., evaporated., and saturated NaHCO3 solution (30 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml), the combined organic layers washed with brine (30 ml) and dried (MgSO4). The crude product was further purified by crystallization (dichloromethane/MeOH/hexane) to yield the title compound (0.11 g, 38%) as a white solid. MS (ISP) 280.0 [(M−H)−]; mp 170° C.

Provenance & Evidence