2-Aminothiazole → Ethyl 6-methylimidazo[2,1-b]thiazole-5-carboxylate

Participants

Reaction Steps

A mixture of 2-aminothiazole (5.0 g. 49.931 mmol) and ethyl 2-chloroacetoacetate (11.5 g, 69.965 mmol) in absolute ethanol (50 mL) was refluxed for 24 h under stirring. The solvent was evaporated under vacuum and the residue was triturated with water (150 mL). The resulting solid was filtered, and dried to give crude product which was further purified by column chromatography to give 3.15 g of the product as an off-white solid; 1H NMR (300 MHz, CDCl3) δ 1.41 (t, J=6.9 Hz, 3H), 2.61 (s, 3H), 4.38 (q, J=6.6 Hz, 2H), 7.41 (d, J=4.2 Hz, 1H), 8.05 (d, J=4.5 Hz, 1H); ESI-MS (m/z) 211.30 (MH)+.

Provenance & Evidence