反应详情

Distilled THF (25 mL) was added to 3-chloro-3-(4-chlorophenyl)-3H-isobenzofuran-1-one (1.042 g, 3.84 mmol) followed by triethylamine (777.1 mg, 7.68 mmol, 1.06 mL)) and benzylamine (616 mg, 5.76 mmol, 0.79 mL) resulting in the formation of a yellow/cream precipitate. The mixture was stirred at room temperature under nitrogen for 4 hours and monitored by TLC. Upon completion the mixture was then extracted with EtOAc (15 mL) and washed with saturated sodium bicarbonate (3×10 mL), water (3×10 mL) and dried (Na2SO4). Recrystallisation of the cream precipitate from a minimum amount of boiling ethyl acetate and excess petrol to yielded the title product as a white crystalline solid (1.0378 g, 2.96 mmol, 77% yield). 1H NMR: (300 Hz, CDCl3) δ ppm 4.24 (d, 1H, J=15.48 Hz, H9), 4.42 (d, 1H, J=15.48 Hz, H9′), 7.16 (m, 5H, H10-H14), 7.25 (m, 5H, H1-H5), 7.56 (m, 2H, H6-H7), 7.75 (d, 1H, H8). 13C NMR: (75 Hz, DMSO); δ 42.80 (N—CH2), 90.60 (O—C—N), 122.95, 123.18, 126.78, 128.07, 128.35, 128.41, 128.51, 129.70, 130.81, 132.97, 133.07, 138.42, 139.46, 149.59 (Ar), 167.20 (C═O). IR: 1463, 1664, 2936, 3285 cm−1.

1. distillationDistilled THF (25 mL)
2. customresulting in the formation of a yellow/cream precipitate
3. extractionUpon completion the mixture was then extracted with EtOAc (15 mL)
4. washwashed with saturated sodium bicarbonate (3×10 mL), water (3×10 mL)
5. dry with materialdried (Na2SO4)
6. customRecrystallisation of the cream precipitate from a minimum amount of boiling ethyl acetate and excess petrol