Trifluoromethanesulfonic anhydride → HCID 118162075, compound

Participants

Reaction Steps

To a solution of N-(3-cyanomethyl-phenyl)-acetamide (500 mg, 2.87 mmol) in anhydrous acetonitrile (5 mL) was added trifluoromethanesulfonic anhydride (1.62 g, 5.74 mmol) slowly at −5° C. The resulting mixture was stirred for 5 min, trimethylsilylazide (1.32 g, 11.48 mmol) was added slowly keeping the temperature below −5° C. The resulting mixture was stirred at −5° C. for 1 h. The reaction was poured into cooled aqueous ammonia chloride and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate and concentrated to give the crude product, which was purified by silica gel column chromatography (1-2% MeOH in DCM) to afford the title compound (260 mg, 1.31 mmol, 45% yield) as a yellow solid. MS (ESI) m/z 199.9 [M+H]+.

Provenance & Evidence