1,3-Dichloroacetone → 4-chloromethyl-2-[(E)-styryl]thiazole

Reaction equation

[C:1]([NH2:11])(=[S:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:12][CH2:13][C:14]([CH2:16]Cl)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:12][CH2:13][C:14]1[N:11]=[C:1](/[CH:2]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[S:10][CH:16]=1

Participants

Procedure

A mixture of thiocinnamamide (11.7 g), 1,3-dichloro-acetone (9.1 g) and ethanol (145 ml) was stirred for one hour under reflux. The reaction mixture was poured into ice-water, which was neutralized with potassium carbonate, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The concentrate was purified by means of column chromatography on silica gel. From the fraction eluted with ether-hexane (1:6, v/v), was obtained 4-chloromethyl-2-[(E)-styryl]thiazole (9.4 g, 56%), which was recrystallized from ether-hexane to yield colorless plates, m.p.88-89° C.