N-Methylaniline → 2-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazoline

Participants

Reaction Conditions

Reaction Steps

A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline hydrochloride (1.47 g, 5.0 mmol), triethylamine (2 ml) and N-methylaniline (1.29 g, 12.0 mmol) in N,N-dimethylformamide (10 ml) charged in a reaction flask was reacted with tetrafluoroethylene, which was made to flow into the flask (ca. 0.7 liter/hr), with vigorous stirring at 80° C. for 30 hours. After cooling to an ambient temperature, the reaction mixture was poured intoa saturated aqueous sodium hydrogencarbonate solution (100 ml), and extracted twice with toluene (100 ml×2). The combined toluene layer was washed twice with 10% hydrochloric acid (50 ml×2) and water (70 ml) and then brine (70 ml), and dried over anhydrous 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 (0.45 g, 1.34 mmol, yield 27%).

Provenance & Evidence