反应详情

To a suspension of 22.8 g (80.0 mmol) of 1-(2,6-diethylphenyl)-3-methylamidinourea hydrochloride in CH3CN (100 ml) were added 19.1 g (160.0 mmol) of DMF-DMA and the reaction mixture was heated at reflux for 3 hours. The CH3CN was removed under reduced pressure and the residue partitioned between CHCl3 and H2O. The layers were separated and the aqueous layer extracted with CHCl3 (1×100). The combined CHCl3 extracts were washed with H2O (1×100 ml), dried (MgSO4) and concentrated under reduced pressure to give an off-white solid, which by NMR confirmed the desired free base. The solid was dissolved in CH3OH and acidified with HCl/MeOH and the MeOH removed under reduced pressure to give an off-white solid which was crystallized from CH3CN to give after vacuum drying (105° C., house vacuum) 16.7 g of crude product. The material was recrystallized from CH3CN (a hot filtration was necessary to remove some undissolved solid) to give 11.0 g of desired product as a white crystalline solid:

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 3 hours
3. customThe CH3CN was removed under reduced pressure
4. customthe residue partitioned between CHCl3 and H2O
5. customThe layers were separated
6. extractionthe aqueous layer extracted with CHCl3 (1×100)
7. washThe combined CHCl3 extracts were washed with H2O (1×100 ml)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated under reduced pressure
10. customto give an off-white solid, which by NMR
11. customthe MeOH removed under reduced pressure
12. customto give an off-white solid which
13. customwas crystallized from CH3CN
14. customto give after vacuum
15. dry with materialdrying (105° C., house vacuum) 16.7 g of crude product
16. customThe material was recrystallized from CH3CN (
17. filtrationa hot filtration
18. customto remove some undissolved solid)