Triethylamine → 1-[(E)-3-(3-Chloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

Participants

Reaction Conditions

Reaction Steps

A solution of 20.00 g (109.52 mmol) of (E)-3-chlorocinnamic acid in 500 ml of dichloromethane was treated at RT with 6 drops of DMF. 10.08 ml (115.00 mmol) of oxalyl chloride in 60 ml dichloromethane were added dropwise and stirring was continued for 3 h30. The solution was evaporated, redissolved in 400 ml of dichloromethane, cooled (0° C.) and treated with a solution of 12.50 g (109.52 mmol) of [1,4]diazepan-5-one and 30.49 ml (219.05 mmol) of triethylamine in 190 ml of dichloromethane. The reaction was warmed up over night to RT and then evaporated. The precipitate was suspended in 90 ml of water, stirred 30 min, and filtered, washed with water to give, after drying under reduced pressure overnight, 28.03 g (92%) of the titled compound as a off-white powder. MS: 278.9 (MH+, 1Cl).

Provenance & Evidence