Imidazole → 1-Benzylimidazole

HRID 1773051Notes

Reaction equation

HRID 1773051 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:6](Cl)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[K+]>C1COCC1>[CH2:6]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 7503Benzyl ChlorideHCID 14797Potassium Hydroxide

Product 1

HCID 779181-BenzylimidazoleYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the selected experimental protocol, 44 g of imidazole (0.65 mol.), 100 g of benzyl chloride (0.78 mol.), and 60 g of KOH (1.07 mol.) in 700 ml of THF are placed in a 1-liter balloon flask. The reaction mixture is brought to reflux for 120 h, then cooled at ambient temperature. The organic phase is filtered and the solvent is evaporated under reduced pressure. The obtained solid product is dissolved in 500 ml of CH2Cl2, then washed with water (3×100 ml). The organic phase is dried on Na2SO4, filtered, then evaporated under reduced pressure. The collected solid is recrystallized in toluene to yield 67 g of desired product.

Workup

  1. customare placed in a 1-liter balloon flask
  2. temperatureto reflux for 120 h
  3. filtrationThe organic phase is filtered
  4. customthe solvent is evaporated under reduced pressure
  5. dissolutionThe obtained solid product is dissolved in 500 ml of CH2Cl2
  6. washwashed with water (3×100 ml)
  7. customThe organic phase is dried on Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe collected solid is recrystallized in toluene

Sources & evidence

ORD record
ord-240dd4688a2d482e820a81d8fea7ac58
Source dataset
uspto-grants-2016_02
Patent number
US09252446B2

Reaction notes

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