Ethyl Acetate → Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate

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Reaction Steps

A solution of ethyl 2-chloro-3-oxo-3-phenylpropanoate (Example 23, 9.73 mmol) and thiourea (9.73 mmol) in EtOH (25 mL) was heated at reflux overnight. The resulting mixture was concentrated in vacuo, neutralized with 18M—NH4OH, and extracted with CH2Cl2. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to afford a yellow solid that was washed with MeOH (3 mL) and dried to afford the product in 89% yield as a pale yellow solid. MH+=249.1, Rf=0.29 (Hexanes:EtOAc=1:1). MH+=249.1, retention time (LC-MS)=2.37 min.

Provenance & Evidence