Thionyl Chloride → 4-(Chloromethyl)-2-(trifluoromethyl)-1,3-thiazole

Participants

Reaction Steps

In chloroform (10 ml) was dissolved 2-trifluoromethyl-4-hydroxymethylthiazole (1 g), to which was added dropwise thionyl chloride (2.0 ml). The mixture was refluxed for 4 hours. The reaction mixture was cooled and, then, excess volume of thionyl chloride was distilled off under reduced pressure. To the residue was added dichloromethane (30 ml), which was washed with an aqueous solution of sodium hydrogen carbonate (20 ml) and water (20 ml), successively, followed by drying over magnesium sulfate. The solvent was distilled off, and the residue was subjected to a silica gel chromatography (2.5×20 cm), eluting with ethyl acetate-hexane (1:3). The desired fraction was concentrated to give 2-trifluoromethyl-4-chloromethyl thiazole (0.66 g) as a pale reddish oily product.

Provenance & Evidence