反应详情

温度

75 °C

3-Trifluoromethylphenylthiourea (12.8 g, 87 mmol), 2-bromo-4-cyanobenzaldehyde (18.3 g, 87 mmol), and methyl acetoacetate (10.4 mL, 96 mmol) were dissolved in THF (300 mL) under an atmosphere of N2 and then trimethylsilylphosphate (18 g) in THF (50 mL) was added, and the mixture heated at 75° C. After 17 hours the reaction mixture was allowed to cool, poured onto 0.5 M HCl (600 mL) and stirred for 30 minutes. The mixture was extracted into EtOAc. The organic phase was washed with water, then brine and dried (Na2SO4) before being concentrated in vacuo. The resulting solid was triturated with Et2O (50 mL), filtered and the solid collected to yield the title compound as a white solid (22.2 g).

1. temperatureto cool
2. extractionThe mixture was extracted into EtOAc
3. washThe organic phase was washed with water
4. dry with materialbrine and dried (Na2SO4)
5. concentrationbefore being concentrated in vacuo
6. customThe resulting solid was triturated with Et2O (50 mL)
7. filtrationfiltered
8. customthe solid collected