反应详情

To a stirred suspension of 7.3 g (30.0 mmol) of methylguanidine sulfate in THF (100 ml) was added 4.8 g (60.0 mmol) of 50% W/W aqueous NaOH. The mixture was stirred for one hour after which 5.0 g of anhydrous Na2SO4 was added and the mixture stirred for an additional hour. To the mixture was added dropwise over one hour a solution of 5.7 g (30.0 mmol) of 2,6-diethylphenylisothiocyanate in THF (40 ml) and the mixture was stirred for two hours at ambient temperature. The THF was removed under vacuum and the residue partitioned between H2O and CHCl3. The layers were separated and the aqueous layer extracted with CHCl3 (1×100 ml). The extracts were dried (MgSO4) and concentrated to give a yellow oil which was dissolved in MeOH and acidified with HCl/MeOH. The MeOH was removed under vacuum to give a viscous yellow oil which slowly crystallized on standing. Crystallization from MeOH/CH3C≡N gave 8.5 g (94 %) of the desired salt.

1. additionwas added
2. stirringthe mixture was stirred for two hours at ambient temperature
3. customThe THF was removed under vacuum
4. customthe residue partitioned between H2O and CHCl3
5. customThe layers were separated
6. extractionthe aqueous layer extracted with CHCl3 (1×100 ml)
7. dry with materialThe extracts were dried (MgSO4)
8. concentrationconcentrated
9. customto give a yellow oil which
10. customThe MeOH was removed under vacuum
11. customto give a viscous yellow oil which
12. customslowly crystallized
13. customCrystallization from MeOH/CH3C≡N