3-Aminopropionitrile → N-(2-cyanoethyl)-2,2-bisfluoromethyl-6-trifluoromethyl-2H-1-benzopyran-4-carbothioamide

Participants

Reaction Steps

O-methyl 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carbothioate (0.34 g) and DBU (10 mg) were dissolved in tetrahydrofuran (5 ml); to the solution, 3-aminopropionitrile (0.2 ml) was added at room temperature in a nitrogen atmosphere and the resulting mixture was stirred for 7 hours at room temperature. Ethyl acetate was added to the reaction mixture, which was washed with water, dilute HCl, aqueous sodium bicarbonate and a saturated aqueous solution of sodium chloride. The mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; methylene chloride) to give the titled compound (0.33 g), which was identical to the authentic sample.

Provenance & Evidence