2-Benzylphenyl isocyanate → 5,11-dihydro-6H-dibenzo[b,e]azepin-6-one

Participants

Reaction Conditions

Reaction Steps

A suspension of anhydrous aluminum chloride (319 mg, 2.39 mmol) in o-xylene is heated to 110° C. Then, a solution of 2-benzylphenylisocyanate (500 mg, 2.39 mmol) is added dropwise and the brown reaction mixture is kept stirring at 150° C. during 1 h. After cooling to rt, the solvent is evaporated, the residue is dissolved in dichloromethane/methanol (19:1) and filtered through a small plug of silica gel. The solvent is evaporated and the crude product is recrystallized from acetonitrile to give pure subtitle compound as a beige solid (170 mg) in 34% yield (Warawa et al., J. Med. Chem. 2001, 44, 372-389): tR (LC-2) 1.87 min; ESI-MS(+): m/z 210.13 [M+H]+ (calcd 209.24 for C14H11NO).

Provenance & Evidence