Benzene → 3-Chloro-5,11-dihydro-dibenzo[b,e]azepin-6-one

Participants

Reaction Steps

To a mixture of 5-chloro-2-methylphenyl isocyanate (100 μL, 0.73 mmol) in CCl4 (2 mL) was added sulfuryl chloride (118 μL, 0.88 mmol) and 2,2′-azobis(isobutyronitrile) (catalytic amount) and the resulting mixture was refluxed for 20 h. The mixture was allowed to obtain room temperature, then diluted with CH2Cl2, washed with saturated aqueous NaHCO3-solution, dried (Na2SO4) and concentrated. The mixture was taken up in benzene (2 mL) and a mixture of AlCl3 (160 mg, 1.2 mmol) in benzene (1 mL) was added. The resulting mixture was stirred at 80° for 4 h, and then allowed to obtain room temperature. The mixture was filtered through a short column (SiO2, heptane:EtOAc, 1:1) to give 25 mg (14%) of the title compound (189JO59). 1H NMR (CDCl3) δ 8.18 (bs, 1H), 7.92 (dd, 1H, J=1.2, 7.8 Hz), 7.46 (dt 1H, J=1.4, 7.4 Hz), 7.34 (dt, 1H, J=1.2, 7.4 Hz), 7.23 (m, 2H), 7.07 (m, 2H), 3.92 (s 2H). MS (ESI) 244 (MH+)

Provenance & Evidence