反应详情

2-Hydrazino-3-nitropyridine (95.2 g, 0.618 mol) was combined with acetonitrile (1 L) and carbon disulfide (114 mL, 143.9 g, 1.89 mol) was added. The resulting mixture was stirred for 1.5 hours. Hydrogen peroxide (78.6 mL of 30 percent aqueous solution, 23.6 g, 0.693 mol) was added dropwise over a 20-min period with cooling at 15°-20° C. The mixture was stirred for another 2 hours and was then cooled in an ice bath. Benzyl chloride (91.7 g, 0.72 mol) was added and then triethylamine (110 mL, 79.6 g, 0.79 mol) was added slowly with stirring over a 2-hour period. The reaction was exothermic. The mixture was stirred at room temperature over the weekend. The volatiles were removed by evaporation under reduced pressure and the residue obtained was diluted with dichloromethane and water. The resulting mixture was filtered through Celite® to remove the precipitated sulfur. The organic phase of the filtrate was recovered, washed with water, and concentrated by evaporation under reduced pressure. The solid residue obtained was diluted with hexane, recovered by filtration, and dried to obtain 174.0 g (98 percent of theory) of the title compound as a brown powder melting at 125°-126° C. (d).

1. additionwas added
2. temperaturewith cooling at 15°-20° C
3. stirringThe mixture was stirred for another 2 hours
4. temperaturewas then cooled in an ice bath
5. stirringwith stirring over a 2-hour period
6. stirringThe mixture was stirred at room temperature over the weekend
7. customThe volatiles were removed by evaporation under reduced pressure
8. customthe residue obtained
9. filtrationThe resulting mixture was filtered through Celite®
10. customto remove the precipitated sulfur
11. customThe organic phase of the filtrate was recovered
12. washwashed with water
13. concentrationconcentrated by evaporation under reduced pressure
14. customThe solid residue obtained
15. filtrationrecovered by filtration
16. customdried