Benzylamine → 4-diethoxyphosphinylmethyl-N-benzylbenzamide

Participants

Reaction Steps

To a solution of 1.36 g of 4-diethoxyphosphinylmethylbenzoic acid and 0.54 g of benzylamine in 15 ml of dry DMF was added dropwise a solution of 1.00 g of diethyl phosphorocyanidate in 2 ml of dry DMF under ice-cooling with stirring. Then, a solution of 0.56 g of triethylamine in 3 ml of dry DMF was added dropwise thereto requiring 5 minutes. The mixture was stirred for 30 minutes under ice-cooling and one hour at room temperature. After adding 30 ml of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water two times. After drying over anhydrous sodium sulfate, the solvent was evaporated. The residue was subjected to silica gel column chromatography (eluent; chloroform:ethyl acetate=1:1), and 4-diethoxyphosphinylmethyl-N-benzylbenzamide was obtained. It was recrystallized from benzene-n-hexane to give 1.60 g of colorless needles.

Provenance & Evidence