Imidazole → 4-((1H-imidazol-1-yl)methyl)-2-methylbenzonitrile

HRID 1881038Notes

Reaction equation

HRID 1881038 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.Br[CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([CH3:22])[CH:15]=1>C1COCC1>[N:7]1([CH2:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([CH3:22])[CH:15]=2)[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 226159811001055-64-6

Product 1

HCID 575175254-((1H-imidazol-1-yl)methyl)-2-methylbenzonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of potassium carbonate (2.16 g,15.7 mmol) in THF at room temperature was added imidazole (4.27 g, 62.8 mmol). The mixture was stirred at room temperature for 10 minutes then 4-(bromomethyl)-2-methylbenzonitrile (CAS 1001055-64-6) (6.6 g, 31.4 mmol) was added and refluxed for 24 hours. The mixture was then cooled to room temperature. Potassium carbonate was filtered off. The filtrate was concentrated and residue was redissolved in dichloromethane. The dichloromethane phase was washed with water (three times) and then HCl (three times). To the combined HCl phase was added sodium carbonate (solid) and extracted with ethyl acetate. Ethyl acetate phase was washed with water and brine, dried over sodium sulfate and concentrated. Column chromatography (10% methanol/ethyl acetate) gave 4-((1H-imidazol-1-yl)methyl)-2-methylbenzonitrile (3.59 g, 58%) as a white solid.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationPotassium carbonate was filtered off
  4. concentrationThe filtrate was concentrated
  5. dissolutionresidue was redissolved in dichloromethane
  6. washThe dichloromethane phase was washed with water (three times)
  7. additionTo the combined HCl phase was added sodium carbonate (solid)
  8. extractionextracted with ethyl acetate
  9. washEthyl acetate phase was washed with water and brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-928ce50f3b9e4b39874ebc7099f8282b
Source dataset
uspto-grants-2012_11
Patent number
US08318783B2

Reaction notes

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