3-Aminopropionitrile → 2,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide

Participants

Reaction Steps

To an ice-cooled mixture of 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxylic acid (0.20 g) and tetrahydrofuran (3 ml), N,N′-carbonyldiimidazole (0.12 g) was added with stirring and the mixture was stirred for 1 hour. Thereafter, 2-cyanoethylamine (0.06 g) was added and the mixture was stirred first under cooling with ice for 1 hour, then at room temperature for 12 hours. To the reaction mixture, an aqueous solution of potassium carbonate was added, followed by extraction with methylene chloride; the organic layer was washed with water and dried; the solvent was distilled off and the resulting residue was recrystallized with a solvent consisting of a mixture of ethyl acetate and hexane, thereby giving the titled compound (0.20 g) having a melting point of 135-136° C.

Provenance & Evidence