Imidazole → 1-Benzylimidazole

HRID 1646427Notes

Reaction equation

HRID 1646427 reaction equation
[OH-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[CH2:8](Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH2:8]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 779181-Benzylimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

260 ml of 50% strength sodium hydroxide solution, 102 g (1.5 mol) of imidazole and 18 g (0.11 mol) of 1-benzimidazole were introduced into a 1 1 four-neck flask with stirrer, thermometer, dropping funnel and reflux condenser, and 209 g (1.65 mol) of benzyl chloride were added dropwise at 50° C., cooling with a water bath. After the addition was complete, the mixture was stirred at 50° C. for 30 min. and then diluted with 350 g of water in order to dissolve the salts completely. The organic phase was then separated off, the aqueous phase was extracted with toluene, and the combined organic phases were dried over sodium sulfate. Removal of the toluene was followed by distillation under reduced pressure. 243 g of 99% pure 1-benzylimidazole (yield 222 g (94%) after subtraction of the product employed as catalyst) of boiling point 132°-135° C. under 0.5 mbar were obtained.

Workup

  1. temperaturereflux condenser
  2. temperaturecooling with a water bath
  3. additionAfter the addition
  4. dissolutionto dissolve the salts completely
  5. customThe organic phase was then separated off
  6. extractionthe aqueous phase was extracted with toluene
  7. dry with materialthe combined organic phases were dried over sodium sulfate
  8. customRemoval of the toluene
  9. distillationwas followed by distillation under reduced pressure
  10. customwere obtained

Sources & evidence

ORD record
ord-e7f1540bd3e541808736e7fd3be3ecaa
Source dataset
uspto-grants-1993_01
Patent number
US05179210

Reaction notes

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