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-dichloroacetone (9.10 g) and ethanol (145 ml) was heated for one hour under reflux. The reaction mixture was poured onto ice-water, neutralized with potassium carbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with diethyl ether-hexane (1:5, v/v), 4-chloromethyl-2-[(E)-2-phenylethenyl]thiazole (9.40 g, 66%) was obtained. Recrystallization from diethyl ether-hexane gave colorless plates, mp 88-89° C.