Methane → Iminostilbene N-carbonylchloride

Participants

Reaction Steps

To a slurry of 14.10g (0.073 mole) of dibenz[b,f]azepine in 60ml of dry toluene at room temperature was added dropwise a 120ml solution of 12.5% phosgene (excess) in benzene over 45 minutes. The resulting yellow slurry was stirred for 2 hours at room temperature, heated to reflux an additional 2 hours, and then stirred at room temperature overnight. Concentration of the reaction mixture by rotary evaporator in the hood gave a pale yellow solid which was taken up in 200ml benzene and treated with Norit-AR at boiling. The hot solution was filtered through celite, concentrated to one half of its original volume, cooled to room temperature and petroleum ether added to turbidity; white crystals of the named product precipitated. Yield, 14.4g, m.p. 145°-150°. Recrystallization from benzene-hexane afforded needles m.p. 150°-156.5°.

Provenance & Evidence