Water → 2-Acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

Participants

Reaction Steps

To a stirred solution of 2-amino-2-methyl-1-propanol (1.14 g, 13 mmol) in dioxane (20 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methylthiazole-5-sulfonyl chloride (2.95 g, 12 mmol) and triethylamine (1.78 ml, 13 mmol). The light yellow suspension was stirred at room temperature for 17 h, poured into water (100 ml) and extracted with dichloromethane (2×10 ml). The combined organic layers were washed with sat. NaHCO3 solution (2×70 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate/MeOH 9:1) and subsequent crystallization (ethyl acetate/MeOH/heptane) to yield 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (1.15 g, 32%) as a light brown solid. MS (ISP) 306.1 [(M−H)−]; mp 194° C.

Provenance & Evidence