反应详情

To a solution of 2-amino-N-(4-bromophenyl)-3-chlorobenzamide (0.52 g, 1.60 mmol) and 4-(2-hydroxyethoxy)-3,5-dimethylbenzaldehyde (0.31 g, 1.60 mmol) in anhydrous ethanol (20 mL), anhydrous copper (II) chloride (0.86 g, 6.40 mmol) was added and the reaction mixture was refluxed for 16 hours. The solvent was evaporated in vacuo, water (100 mL) was then added, and the product was extracted with ethyl acetate (200 mL). The organic phase was separated, washed with water (2×100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. The solvent was evaporated, and the crude compound was purified by the Simpliflash system (20-40% ethyl acetate in hexanes as eluent), to give the title compound as a white solid. Yield 0.37 g (46%). MP 185-186° C. 1H-NMR (400 MHz, CDCl3) 8.25 (d, J=8.20 Hz, 1H) 7.89 (d, J=7.42 Hz, 1H) 7.56-7.34 (m, 3H) 7.03 (t, J=4.29 Hz, 4H), 4.06-3.87 (m, 2H) 3.87-3.74 (m, 2H) 2.18 (s, 6H) 2.11-1.95 (m, 1H). MS (ES+) m/z: 499.36, 501.38 (100%), 503.33.

1. temperaturethe reaction mixture was refluxed for 16 hours
2. customThe solvent was evaporated in vacuo, water (100 mL)
3. additionwas then added
4. extractionthe product was extracted with ethyl acetate (200 mL)
5. customThe organic phase was separated
6. washwashed with water (2×100 mL)
7. dry with materialbrine (100 mL), and dried over anhydrous Na2SO4
8. customThe solvent was evaporated
9. customthe crude compound was purified by the Simpliflash system (20-40% ethyl acetate in hexanes as eluent)