Imidazole → 4-(1-Imidazolylmethyl)benzonitrile

HRID 35905Notes

Reaction equation

HRID 35905 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[H][H].Br[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1>CN(C)C=O.C(OCC)(=O)C.O>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 111481024-(1-Imidazolylmethyl)benzonitrileYield 71.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under cooling, 23.15 g of imidazole in 250 ml of N,N-dimethylformamide is combined in portions with 14.8 g of sodium hydride, 60% in oil, and stirred for 1.5 hours at 25° up to the end of hydrogen release. In two portions, 50 g of 4-(bromomethyl)benzonitrile is added under ice cooling to this solution and the mixture is agitated for 1.5 hours at 25° . For processing, 100 ml of water is added under ice cooling, the mixture is agitated for 0.25 hour, poured into 1.5 1 of ethyl acetate, washed neutral with water, washed twice with sodium chloride and water, dried over sodium sulfate, concentrated to dryness under vacuum, and crystallized from acetone/diethyl ether, thus obtaining 33.6 g of 4-[1-(imidazolyl)methyl]benzonitrile as colorless crystals, mp 102°.

Workup

  1. temperatureUnder cooling
  2. stirringthe mixture is agitated for 0.25 hour
  3. washwashed neutral with water
  4. washwashed twice with sodium chloride and water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under vacuum
  7. customcrystallized from acetone/diethyl ether

Sources & evidence

ORD record
ord-1acfe0db10aa47458aed8cc6de7991b2
Source dataset
uspto-grants-1995_05
Patent number
US05411982

Reaction notes

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