Bis-(1H-imidazol-2-YL)-methanone → 4,5-Dichloronicotinonitrile

HRID 2264920Notes

Reaction equation

HRID 2264920 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

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 723354613-Pyridinecarboxaldehyde, 4,5-dichloro-, oxime

Product 1

HCID 197757134,5-DichloronicotinonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturebefore cooling
  4. washthen washing with saturated aqueous sodium bicarbonate (70 ml) and water (70 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification of the resultant residue by flash chromatography (Si-PPC, cyclohexane:dichloromethane gradient 20:80 to 0:100)

Sources & evidence

ORD record
ord-cd27e7b9a2af4a339ae71c77bc902ddf
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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