反应详情

Potassium carbonate (4.34 g, 31.4 mmol) and benzamidine (2.59 g, 21.5 mmol) were added at to a suspension of 2-(2,4-dichloro-benzylidene)-malononitrile (4 g, 17.9 mmol) in methanol. The yellow mixture was stirred for 1 h at room temperature and then heated to reflux for an additional 2 h. After cooling, the solvent was removed at reduced pressure, the residue was taken up in ethyl acetate/ice. The organic phase was separated, washed with water, and dried over sodium sulfate. The solvent was evaporated, the orange residue was taken up in acetone, and 1.91 g potassium manganate was added. After stirring for 90 min, the reaction mixture was filtered through decalite and evaporated. Purification by flash chromatography (silica gel, EtOAc/hexanes) afforded the title compound, MS: m/e=340.8 (M+), as a solid (2.63 g, 43%).

1. temperatureheated
2. temperatureto reflux for an additional 2 h
3. temperatureAfter cooling
4. customthe solvent was removed at reduced pressure
5. customThe organic phase was separated
6. washwashed with water
7. dry with materialdried over sodium sulfate
8. customThe solvent was evaporated
9. addition1.91 g potassium manganate was added
10. stirringAfter stirring for 90 min
11. filtrationthe reaction mixture was filtered through decalite
12. customevaporated
13. customPurification by flash chromatography (silica gel, EtOAc/hexanes)