Bis-(1H-imidazol-2-YL)-methanone → 3-Pyridinecarbonitrile, 4-chloro-5-fluoro-

HRID 2264929Notes

Reaction equation

HRID 2264929 reaction equation
[Cl:1][C:2]1[C:7]([F: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[F:8]

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 597047734-Chloro-5-fluoro-pyridine-3-carbaldehyde oxime

Product 1

HCID 595964283-Pyridinecarbonitrile, 4-chloro-5-fluoro-Yield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-5-fluoro-pyridine-3-carbaldehyde oxime (6.8 g, 39.0 mmol) in dichloromethane (150 ml) was added carbonyl diimidazole (9.5 g, 58.5 mmol). The mixture was then heated at reflux for 30 minutes before cooling to room temperature, before being washed with saturated aqueous sodium bicarbonate followed by water. The organic layer was dried over sodium sulfate and concentrated in vacuo and the resultant residue triturated in diethyl ether/cyclohexane to afford the title compound as a pale yellow solid (4.05 g, 79%). 1H NMR (CDCl3) 8.71 (1H, d, J=0.4 Hz), 8.70 (1H, s).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 30 minutes
  3. washbefore being washed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe resultant residue triturated in diethyl ether/cyclohexane

Sources & evidence

ORD record
ord-e07fe614c1ff49cf9ea3eb47661db4cf
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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