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

HRID 2092185Notes

Reaction equation

HRID 2092185 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-c0c4cfe101fb47f9bfb0e32ad6e1e3c3
Source dataset
uspto-grants-2013_05
Patent number
US08440698B2

Reaction notes

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