Pyridine → Iminostilbene N-carbonylchloride

Participants

Reaction Steps

A solution of 2.8 g of iminostilbene (34) in 100 mL of dichloromethane was treated with 1.5 g of triphosgene followed by 3 mL of pyridine and stirred at room temperature overnight. Thin layer chromatography in 40% ethyl acetate-hexane indicated formation of one product. The reaction mixture was washed with water and concentrated in vaccuo. The residue was chromatographed on silica using 10% ether/dichloromethane to yield 3.2 g of 5H-dibenz[b,f]azepine-5-carbonylchloride (35) as an off-white powder. NMR, IR and MS data confirmed the compound identity.

Provenance & Evidence