Thionyl Chloride → 5-Chloromethyl-2-(4-chlorophenyl)thiazole
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:13]O)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>ClCCl>[Cl:17][CH2:13][C:10]1[S:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:12][CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of [2-(4-chlorophenyl)thiazol-5-yl]methanol (3.24 g, 14.3 mmol) in dichloromethane (40 ml) is added dropwise the thionyl chloride (1.3 ml, 18 mmol) at room temperature under nitrogen. The reaction mixture is stirred at room temperature for 4 hours. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 5-chloromethyl-2-(4-chlorophenyl)thiazole (3.24 g)