Water → HCID 19956156, compound

Participants

Reaction Steps

Thionyl chloride (80 μl, 1.1 mmol) is added to 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (150 mg, 0.949 mmol) in 5 ml of N,N-dimethylacetamide at -15°/-10° C. and the mixture is stirred at this temperature for one hour. After addition of 2-amino-5-(phenylcarbonyl)thiazole (130 mg, 0.636 mmol) and equilibration to room temperature, the reaction mixture is stirred for 2.5 hours, then poured into 100 ml of water and subjected to extraction with 3×100 ml of ethyl acetate. The combined organic phases are washed with 50 ml of saturated sodium chloride solution, dried over magnesium sulfate and filtered, and the solvent is distilled off. The oil which remains is purified by flash chromatography (eluent: 33% v/v ethyl acetate in petroleum ether (40/60)) to give N-[5-(phenylcarbonyl)thiazol-2-yl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (0.10 g, 46%) as pale yellow crystals. These crystals are digested in dichloromethane.

Provenance & Evidence