Hydrochloric Acid → HCID 57756680, compound

Participants

Reaction Conditions

Reaction Steps

Copper(I) chloride (0.342 g, 3.45 mmol) and t-butyl nitrite (0.52 mL, 4.37 mmol) were stirred in 20 mL of acetonitrile. Ethyl 2-amino-4-({[2-(trifluoromethyl)-phenyl]methyl}oxy)-1,3-thiazole-5-carboxylate (1.00 g, 2.88 mmol) was added, and the reaction was stirred for 1.5 hours. The reaction was heated to 65° C. with an oil bath for an hour and cooled to room temperature. The reaction mixture was slowly pipeted onto 40 mL of 6N HCl stirring at 0° C. The ice bath was removed, and the mixture was warmed to room temperature, where it stirred for 30 minutes. The mixture was poured into ethyl acetate and water, and the layers were separated. The organic layer was washed with brine, and the combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to provide 0.537 g (51%) of ethyl 2-chloro-4-({[2-(trifluoromethyl)phenyl]methyl}oxy)-1,3-thiazole-5-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ 7.88-7.73 (m, 3H), 7.60 (m, 1H), 5.63 (s, 2H), 4.24 (q, J=7.1 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H).

Provenance & Evidence