Ethanol → Ethyl 2-phenylthiazole-5-carboxylate
Reaction equation
[CH:1]([CH:3](Cl)[C:4]([O-:6])=[O:5])=O.[C:8]([NH2:16])(=[S:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:17][CH2:18]O>>[C:9]1([C:8]2[S:15][C:3]([C:4]([O:6][CH2:17][CH3:18])=[O:5])=[CH:1][N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
4
Procedure
A solution of α-formyl-α-chloroacetate (9.34 g, 49.5 mmol, 1 eq) and thiobenzamide (6.79 g, 49.5 mmol, 1 eq) in EtOH (37.0 mL) is refluxed for 1 hr. The solution changes from an orange/brown color to a deep green. This solution is washed with water and extracted with CH2Cl2. The organic fraction is dried over Na2SO4, filtered, and the solvent removed in vacuo. The product is purified by column chromatography using a Biotage Flash 40M column (20% hexanes/EtOAc) to give ethyl 2-phenyl-thiazole-5-carboxylate as a deep orange oil (1.82 g, 15%). MS (ESI) for C12H13NO3S m/z 252.1 (M+H)+.