反应详情

Distilled THF (50 mL) was added to 3-chloro-3-(4-chlorophenyl)isobenzofuran-1(3H)-one (1.50 g, 5.76 mmol) followed by 4-chlorobenzylamine (0.77 mL, 6.34 mmol) and triethylamine (0.96 mL, 6.91 mmol) as for general procedure A and recrystallised in acetonitrile to give pure white solid 2-(4-chlorobenzyl)-3-(4-chlorophenyl)-3-hydroxyisoindolin-1-one (945 mg, 2.46 mmol. 43%). Rf 0.54 (40:60 EtOAc:petrol). Mp. 156.5-157.4° C. λmax (CH3OH)/nm 221.0, Abs 0.850. IR: 3159, 1659, 1487, 1468 cm−1. 1H NMR (300 Hz, CDCl3); δ 3.07 (s, br, 1H, OH), 4.01 (d, 1H, J=15.0 Hz, N—CH2), 4.52 (d, 1H, J=15.0 Hz, N—CH2), 7.05 (m, 4H, Ar—H), 7.16-7.21 (m, 5H, Ar—H), 7.42 (m, 2H, Ar—H), 7.73 (m, 1H, Ar—H). 13C NMR (75 Hz, DMSO); δ 42.6 (N—CH2), 91.5 (Ar2(O)CN), 123.1, 124.0, 128.2, 128.7, 129.1, 130.4, 130.6, 133.4, 133.5, 135.0, 136.8, 137.0, 148.8 (Ar), 168.0 (C═O). LC/MS-ES+ m/z 406.1, 366.0, 244.9, 242.9, 161.0. Anal. Calcd. for C21H15Cl2NO2.0.2H2O: C, 65.03; H, 4.00; N, 3.61%. Found C, 65.08; H, 4.06; N, 3.88%. HRMS (EI) m/z: 244.0291. Found 244.0299.

1. distillationDistilled THF (50 mL)
2. customrecrystallised in acetonitrile