反应详情

温度

-78 °C

2-[(2-cyanopyridin-3-yl)amino]-N,N-dimethylethanesulfonamide (1.4 g, 5.5 mmol) was dissolved in 50 mL MeOH and placed in a 100 mL pressure flask. The solution was cooled to −78° C. and HCl gas was bubbled through the solution until the volume of the solution had noticeably increased. The flask was sealed and the reaction warmed to room temperature and stirred for 4 hours. At this time, LCMS (sampled after re-cooling the reaction to −78° C.) showed only a small amount of starting cyano compound remaining. Water (1 mL, 55 mmol) was added and the reaction transferred to a flask equipped with a reflux condenser. The reaction was refluxed for 1.5 hours, stirred at room temperature overnight, then refluxed for 2 more hours, then stirred at room temperature for 48 hours. The solution was evaporated to dryness to give a green/yellow foam that was then partitioned between CHCl3 and saturated NaHCO3. The layers were separated and the aqueous was extracted circa 10 times or until very little UV-active material was removed. The organic layers were dried over Na2SO4, filtered and evaporated to give the product as a clear oil that solidified upon standing.

1. customplaced in a 100 mL pressure flask
2. customHCl gas was bubbled through the solution until the volume of the solution
3. temperaturehad noticeably increased
4. customThe flask was sealed
5. temperaturethe reaction warmed to room temperature
6. aliquotAt this time, LCMS (sampled
7. temperatureafter re-cooling
8. customthe reaction to −78° C.)
9. customthe reaction transferred to a flask
10. customequipped with a reflux condenser
11. temperatureThe reaction was refluxed for 1.5 hours
12. stirringstirred at room temperature overnight
13. temperaturerefluxed for 2 more hours
14. stirringstirred at room temperature for 48 hours
15. customThe solution was evaporated to dryness
16. customto give a green/yellow foam that
17. customwas then partitioned between CHCl3 and saturated NaHCO3
18. customThe layers were separated
19. extractionthe aqueous was extracted circa 10 times
20. customuntil very little UV-active material was removed
21. dry with materialThe organic layers were dried over Na2SO4
22. filtrationfiltered
23. customevaporated