反应详情

To a suspension of 10.9 g. (40.0 mmol) of 1-(2',6'-dimethylphenyl)-3-methoxyamidinourea in CH3CN (50 ml.) is added 9.5 g. (80.0 mmol) of DMF-DMA and the mixture heated at 105°-110° C. in a closed bomb for 1-1/2 hours. The reaction mixture is cooled and poured into a round bottom flask and the CH3CN removed under reduced pressure. The residue is partitioned between CHCl3 and H2O and the layer separated. The aqueous layer is extracted with CHCl3 (1×75 ml.). The combined organic layers are washed with H2O (1×50 ml.), dried (MgSO4) and concentrated under reduced pressure to give an oily residue. The residue is taken up in Et2O and washed with H2O (2×50 ml.). The Et2O layer is dried (MgSO4) and concentrated under reduced pressure to give a viscous oil. NMR shows that DMF has been removed. The oil is taken up in hot CH3CN cooled and a small amount of CHCl3, H2O and DMSO insoluble material filtered off. The filtrate is concentrated to give a viscous oil. TLC of the oil (Silicagel; 3% NH4OH, iPA) versus starting material shows one spot moves slower than starting material. Upon addition of MEOH and warming on a steam bath the oil solidifies. The solid is crystallized from MeOH to give 4.6 g. (43%) of 1-(2',6'-dimethylphenyl)-4-methoxyamino-1,2-dihydro-1,3,5-triazin-2-one as a white solid, melting point 78°-80° C.

1. additionTo a suspension of 10.9 g
2. temperatureThe reaction mixture is cooled
3. additionpoured into a round bottom flask
4. customthe CH3CN removed under reduced pressure
5. customThe residue is partitioned between CHCl3 and H2O
6. customthe layer separated
7. extractionThe aqueous layer is extracted with CHCl3 (1×75 ml.)
8. washThe combined organic layers are washed with H2O (1×50 ml.)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated under reduced pressure
11. customto give an oily residue
12. washwashed with H2O (2×50 ml.)
13. dry with materialThe Et2O layer is dried (MgSO4)
14. concentrationconcentrated under reduced pressure
15. customto give a viscous oil
16. customhas been removed
17. temperaturecooled
18. filtrationa small amount of CHCl3, H2O and DMSO insoluble material filtered off
19. concentrationThe filtrate is concentrated
20. customto give a viscous oil
21. additionUpon addition of MEOH
22. temperaturewarming on a steam bath the oil
23. customThe solid is crystallized from MeOH
24. customto give 4.6 g