反应详情

To a solution of the aldehyde from Step 1 (1.2 g, 3.6 mmol) in benzene (18 mL) was added ethyl cyanoacetate (0.38 mL, 3.6 mmol), ammonium acetate (50 mg, 0.7 mmol) and glacial acetic acid (0.17 mL, 2.8 mmol). The solution was heated at reflux for 18 hours, cooled, and partitioned between water and ethyl acetate. The organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine. The organic solution was dried and concentrated. The residue was chromatographed on silica (40% hexane in ethyl acetate) to give the desired product (1.0 g, 66%): Anal. calc'd for C21H18N4O4S: C, 59.82; H, 4.30; N, 13.22. Found: C, 59.70; H, 4.29; N, 13.26.

1. temperatureThe solution was heated
2. temperatureat reflux for 18 hours
3. temperaturecooled
4. custompartitioned between water and ethyl acetate
5. washThe organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine
6. customThe organic solution was dried
7. concentrationconcentrated
8. customThe residue was chromatographed on silica (40% hexane in ethyl acetate)