Imidazole → 2-(1H-imidazol-1-yl)benzonitrile

HRID 857706Notes

Reaction equation

HRID 857706 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].F[C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12].C(OCC)(=O)C>CN(C)C=O>[N:1]1([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 678552-Fluorobenzonitrile

Product 1

HCID 1902752-(1H-imidazol-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-imidazole (0.61 g, 9.0 mmol) in dimethylformamide (8 ml) was added sodium hydride (60% in oil, 0.36 g, 9.0 mmol) and the reaction mixture was stirred at room temperature for 40 min. 2-Fluoro-benzonitrile (0.9 ml, 8.2 mmol) was added and the reaction was stirred at room temperature for 45 min, heated to 60° C. for 45 min and then stirred at room temperature overnight. Ethyl acetate was added and the mixture was washed with water and brine. Drying and solvent evaporation gave 2-imidazol-1-yl-benzonitrile; 1H NMR (CDCl3, 400 MHz) δ 7.86 (bs, 1H), 7.84 (m, 1H), 7.75 (m, 1H), 7.54 (m, 1H), 7.47 (dd, 1H, J=8.1 Hz, J=1 Hz), 7.36 (m, 1H), 7.27 (m, 1H).

Workup

  1. stirringthe reaction was stirred at room temperature for 45 min
  2. temperatureheated to 60° C. for 45 min
  3. stirringstirred at room temperature overnight
  4. washthe mixture was washed with water and brine
  5. customDrying
  6. customsolvent evaporation

Sources & evidence

ORD record
ord-3b2442c73d8e46a9b97dc318a20e887f
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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