Trichloroacetonitrile → 2-(trichloromethyl)-1H-imidazole

Participants

Reaction Steps

To a stirred solution of trichloroacetonitrile (28.8 g, 200 mmol, 1 eq) in anhydrous THF (70 mL) at −60° C. under an argon atmosphere, 2,2-dimethoxyethanamine (21.8 mL, 200 mmol, 1.0 eq) was added dropwise over 5 min. The resulting mixture was allowed to warm to RT and stirred at RT for 4 h. The mixture was concentrated in vacuo and the residue was added in portions to a stirred solution of trifluoroacetic acid (100 mL) at −30° C. under argon. The resulting mixture was then stirred from −30° C. to RT overnight. The reaction mixture was concentrated in vacuo to afford 2-(trichloromethyl)-1H-imidazole. The crude product was used in the next step without further purification.

Provenance & Evidence