Bis-(1H-imidazol-2-YL)-methanone → 4,5-Dichloronicotinonitrile
Reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[N:10]O.C(C1NC=CN=1)(C1NC=CN=1)=O>ClCCl>[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[CH:4][N:5]=[CH:6][C:7]=1[Cl:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 4,5-dichloropyridine-3-carbaldehyde oxime (7.84 g, 41.05 mmol) in dichloromethane (150 ml) was added carbonyl diimidazole (7.99 g, 49.26 mmol). The mixture was then heated to reflux for 1.5 hours before cooling then washing with saturated aqueous sodium bicarbonate (70 ml) and water (70 ml). The organic layer was dried over magnesium sulfate and concentrated in vacuo. Purification of the resultant residue by flash chromatography (Si-PPC, cyclohexane:dichloromethane gradient 20:80 to 0:100) afforded the title compound as a white solid (0.53 g, 72%). LCMS (method B): RT=2.86 min, no ion present.