Thioacetamide → Ethyl 2-(2-methylthiazol-5-yl)acetate
Reaction equation
Br[CH:2]([CH:9]=O)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:11]([NH2:14])(=[S:13])[CH3:12]>ClC(Cl)C>[CH3:12][C:11]1[S:13][C:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][N:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 28.7 g of ethyl 3-bromo-4-oxo-butyrate, 300 ml of dichloroethane and 11.2 g of thioacetamide was refluxed for 10 hours with stirring while replacing the dichloroethane that distilled to keep the volume constant and then the mixture was cooled to room temperature. The mixture was evaporated to dryness and the residue was dissolved in ethyl acetate. The solution was extracted with 2N hydrochloric acid and the pH of the aqueous extracts was made alkaline by addition of ammonium hydroxide. The mixture was extracted with ethyl acetate and the organic extract was washed with water, dried and evaporated to dryness to obtain 8.3 g of ethyl 2-methyl-5-thiazole acetate. The IR spectrum in CHCl3 showed ester C=O at 1737cm-1 and C=C and C=N at 1535cm-1.