[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[Cl:16][C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>ClCCl.C(OCC)(=O)C.CCCCCC>[CH:10]1[C:9]2[CH:8]=[CH:7][C:5]3[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=3[N:15]([C:17]([Cl:16])=[O:19])[C:14]=2[CH:13]=[CH:12][CH:11]=1A 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.
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