Amide to Nitrile

(TFAA)

Examples:

Example 1

To a solution of the SM (1.0 g, 4 mmol) in dry DCM (20 mL) at 0 C was added TEA (3.1 g, 31.0 mmol), followed by TFAA (4.1 g, 20.0 mmol). The resulting mixture was allowed to warm to RT and stir for 16 h, after which time it was partitioned between DCM (50 mL) and H2O (50 mL). The org layer was washed with sat aq NaHCO3 (100 mL), dried (Na2SO4), and concentrated in vacuo to provide the product as a thick liquid. [800 mg, 87%]

[Patent Reference: WO2014149164, page 214, (23.7 MB)]

Example 2

To a mixture of the SM (50 mg, 0.13 mmol) and TEA (39 mg, 0.39 mmol) in DCM (4 mL) was added TFAA (55 mg, 0.26 mmol) at RT. The mixture was stirred at RT for 2 h. The mixture was diluted with H2O (5 mL) and DCM (10 mL). The org layer was washed with brine (5 mL), dried (Na2SO4), and concentrated to provide the product. [42 mg, 68%]

[Patent Reference: WO2016011390, page 102, (20.2 MB)]