Dimethylformamide → 2-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazoline

Participants

Reaction Conditions

Reaction Steps

A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1.29 g, 5.0 mmol) and piperidine (0.64 g, 7.5 mmol) in N,N-dimethylformamide (10 ml) was reacted in a reaction flask with tetrafluoroethylene, which was made to flow into the flask (ca. 0.7 liter/hr), with vigorous stirring at 50° C. for 21 hours. After cooling to an ambient temperature, the reaction mixture was poured into ice-water, and extracted with diethyl ether. The diethyl ether layer was washed with water and then brine, and dried over magnesium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography, which afforded 2-difluoroacetylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1.24 g, 3.7 mmol, yield 74%). Unreacted part of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (0.30 g) was recovered.

Provenance & Evidence