Water → HCID 57756685, compound

Participants

Reaction Steps

Ethyl 2-(acetylamino)-4-hydroxy-1,3-thiazole-5-carboxylate (6.04 g, 26.2 mmol) was dissolved in 100 mL of N,N-dimethylformamide with stirring. Potassium carbonate (3.98 g, 28.8 mmol) was added in a single portion. 2-Trifluoromethylbenzyl bromide (6.58 g, 27.5 mmol) in 20 mL of N,N-dimethylformamide was added via syringe. The reaction was stirred for 16 hours and poured into water and ethyl acetate. The layers were separated, and the organic layer was washed with brine. The combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash chromatography afforded 6.23 g (61%) of ethyl 2-(acetylamino)-4-({[2-(trifluoromethyl)-phenyl]methyl}oxy)-1,3-thiazole-5-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ 12.62 (s, 1H), 7.92 (m, 1H), 7.82-7.71 (m, 2H), 7.58 (m, 1H), 5.60 (s, 2H), 4.19 (q, J=7.2 Hz, 2H), 2.17 (s, 3H), 1.25 (t, J=7.2 Hz, 3H).

Provenance & Evidence