Imidazole → 2-(1H-Imidazol-1-ylmethyl)benzonitrile

HRID 1690752Notes

Reaction equation

HRID 1690752 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[C:8]([C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12]Br)#[N:9].O>CN(C=O)C>[N:1]1([CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[C:8]#[N:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 142311482-(1H-Imidazol-1-ylmethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of imidazole (1.0 g, 14.6 mmol) in DMF (10 mL) is added sodium hydride (60% wt. in mineral oil, 0.887 g, 22.17 mmol) at room temperature. The mixture is stirred for 30 min, whereupon 2-cyanobenzyl bromide (2.87 g, 14.6 mmol) is added. After an additional 30 min, water is added and the mixture is extracted with ethyl acetate. The aqueous phase is poured into aqueous sodium bicarbonate and extracted with dichloromethane. The combined organic phase is dried over sodium sulfate, filtered and concentrated in vacuo to give a residue which is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 2-imidazol-1-ylmethyl-benzonitrile; MS (ESI) m/z 184.3 (M+H).

Workup

  1. additionis added
  2. extractionthe mixture is extracted with ethyl acetate
  3. additionThe aqueous phase is poured into aqueous sodium bicarbonate
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue which
  9. customis purified by silica gel chromatography (dichloromethane-methanol, 19:1)

Sources & evidence

ORD record
ord-445a55046a304c6da90d0c7be000f0ab
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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