Acetonitrile → [4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetonitrile

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Reaction Steps

Tetrabutylammonium cyanide (18.5 g, 67 mmol) was added to a solution of 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole [15.0 g, 51 mmol; PCT Int. Appl. (2002), WO 0292590 A1] in acetonitrile (340 ml). The solution was stirred at ambient temperature for 16 h, saturated aqueous sodium bicarbonate solution/ice water 1/1 and ethyl acetate were added and the layers were separated. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with ice water/brine 1/1, dried over sodium sulfate and the solvent was evaporated in vacuo to give a brown oil which was purified by column chromatography (silica gel, n-heptane/CH2Cl2) to yield 8.58 g (30 mmol, 59%) of the title compound as light yellow solid.

Provenance & Evidence