Triethylamine → 5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

Participants

Reaction Steps

To a solution of 1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (0.87 g) and triethylamine (0.55 g) in dichloromethane (5 ml) was added a solution of 4-nitrobenzoyl chloride (1.00 g) in dichloromethane (5 ml) at ambient temperature. After being stirred at ambient temperature for 2 hours, the solution was washed successively with 0.5N hydrochloric acid, saturated sodium bicarbonate aqueous solution, and brine. The organic layer was dried over magnesium sulfate, filtered and the solvents was evaporated. Trituration with a mixture of diethyl ether and diisopropyl ether (1:1) of a crude product afforded 5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (1.60 g) as a slightly brown powder.

Provenance & Evidence