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

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.

1. temperatureThe mixture was refluxed for 4 hours
2. temperatureThe reaction mixture was cooled
3. distillationexcess volume of thionyl chloride was distilled off under reduced pressure
4. additionTo the residue was added dichloromethane (30 ml), which
5. washwas washed with an aqueous solution of sodium hydrogen carbonate (20 ml) and water (20 ml)
6. dry with materialby drying over magnesium sulfate
7. distillationThe solvent was distilled off
8. washeluting with ethyl acetate-hexane (1:3)
9. concentrationThe desired fraction was concentrated

ORD record

ord-7aa45e82ba1342f98966745b882e9d1a

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05405861