Imidazole → 3-(1H-imidazol-1-yl)benzonitrile

HRID 619169Notes

Reaction equation

HRID 619169 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>[Cu].CN(C=O)C>[N:10]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 678803-Fluorobenzonitrile

Product 1

HCID 49612723-(1H-imidazol-1-yl)benzonitrileYield 47.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-fluorobenzonitrile (18 ml, 168.38 mmol), imidazole (11.46 g), K2CO3 (25.59 g), copper (1.75 g), potassium iodide (1.75 g) and DMF (125 ml) was refluxed overnight. The reaction mixture was cooled to room temperature and poured into ice/water (600 ml). A precipitate formed, which was collected by filtration, washed with water, dissolved in ethanol (25 ml)/CHCl3 (500 ml) and filtered. The filtrates were partitioned in water, the organic layer was separated, dried over MgSO4 and stripped. The residue was combined with the product from another experimental run and was recrystallized from CHCl3 /hexanes to afford 13.4 g of 3-(1-imidazolyl)benzonitrile.

Workup

  1. temperaturewas refluxed overnight
  2. customA precipitate formed
  3. filtrationwhich was collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in ethanol (25 ml)/CHCl3 (500 ml)
  6. filtrationfiltered
  7. customThe filtrates were partitioned in water
  8. customthe organic layer was separated
  9. dry with materialdried over MgSO4
  10. customwas recrystallized from CHCl3 /hexanes

Sources & evidence

ORD record
ord-daf1b6eed2f2433f9e539d87fdd08975
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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