反应详情

A solution of 2.4 g of (8) (0.010 mol) in 100 ml of CH2Cl2 was cooled to 0° C. as 2 ml of thionyl chloride in 5 ml of CH2Cl2 was added dropwise. The cooling was removed, the reaction stirred for 1.5 h, then heated to reflux for 45 min. Upon cooling to ambient temperature, ice-water was added to the reaction, followed by enough saturated aqueous K2CO3 to make the reaction basic. The mixture was extracted 3× with 25 ml of CH2Cl2, the extracts washed with brine, dried, and the solvent evaporated. The residue was purified by radial chromatography eluting with 2.5% ethanol-0.25% NH4OH-CHCl3 to give 1.74 g of (12). Recrystallization from hexane gave colorless crystals, mp 59°-60° C. NMR ppm (CDCl3) 1.5 (1H, bs), 1.65 (2H, m), 2.35 (1H, m), 2.7 (2H, m) 2.97 (1H, m), 3.15 (2H, m), 3.65 (1H, m), 4.03 (1H, bm), 4.07 (3H, s), 8.1 (2H, m). Anal. C12H16ClN3O requires C: 56.81; H: 6.36; N: 16.56%. Found C: 56.63; H: 6.41; N: 16.48%. Further elution with 5% ethanol-0.5%NH4OH-CHC13 gave 0.13 g of (11), identical to the material produced previously.

1. additionwas added dropwise
2. customThe cooling was removed
3. temperatureheated
4. temperatureto reflux for 45 min
5. additionice-water was added to the reaction
6. extractionThe mixture was extracted 3× with 25 ml of CH2Cl2
7. washthe extracts washed with brine
8. customdried
9. customthe solvent evaporated
10. customThe residue was purified by radial chromatography
11. washeluting with 2.5% ethanol-0.25% NH4OH-CHCl3