2-Benzylphenyl isocyanate → 5,11-dihydro-6H-dibenzo[b,e]azepin-6-one
反応式
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]=[O:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CC1C=CC=CC=1C>[CH:17]1[C:12]2[CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:19](=[O:20])[NH:18][C:13]=2[CH:14]=[CH:15][CH:16]=1参加物
4
反応条件
- 温度
- 110 °C
実験手順
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).