Potassium Cyanide → 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one
Reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:16](Cl)=[C:15]([C:18]#[N:19])[N:14]([CH2:20][CH2:21][CH3:22])[C:13]2=[O:23])=[C:4]([F:24])[CH:3]=1.[C-:25]#[N:26].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:16]([C:25]#[N:26])=[C:15]([C:18]#[N:19])[N:14]([CH2:20][CH2:21][CH3:22])[C:13]2=[O:23])=[C:4]([F:24])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The product of Example 4, 1-(4-chlorophenyl)-5-chloro-4-cyano-3-phenyl-1,3-dihydro-2H-imidazol-2-one (V) (0.94 g, 2.8 mmol) was stirred in 25 mL dimethylformamide. To this mixture was added KCN (0.6 g, 8.5 mmol) and the resulting mixture was heated to reflux for ten minutes. The mixture was then allowed to cool, poured onto water, extracted with ethyl acetate, dried, filtered, and evaporated via standard techniques. Recrystallization with ethyl acetate/heptane gave 0.5 g of 1-(4-chlorophenyl)-4,5-dicyano-3-phenyl-1,3-dihydro-2H-imidazol-2-one (VI) as an orange solid (m.p. 182°-4° C.).