Imidazole → 1-Phenethylimidazole

HRID 1388511Notes

Reaction equation

HRID 1388511 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(=O)(O)[O-].[Na+].O>CO>[C:4]1([CH2:3][CH2:2][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 7666Phenethyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 102196211-Phenethylimidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2-Bromoethyl)benzene (41.62 g, 0.225 mol) was added dropwise to a stirred mixture of imidazole (13.6 g, 0.2 mol) and sodium bicarbonate (16.8 g, 0.2 mol) in methanol (100 ml). Following the addition, the reaction mixture was stirred at ambient temperature for 24 h, and then stirred and heated under reflux for 6 h. After concentration of the reaction mixture under reduced pressure, the residue was treated with water (100 ml), and this mixture was extracted with chloroform (3×75 ml). The combined extracts were dried (magnesium sulphate), and the solution was then evaporated under reduced pressure. The resulting brown oil was distilled to afford 1-(2-phenylethyl)imidazole, b.p. 122°/0.2 mmHg. The slightly impure product was purified using a silica gel column and by elution with ethyl acetate/methanol (9:1). The product fractions were pooled, concentrated, under reduced pressure, and then distilled, to afford the pure product, b.p. 110°/0.1 mmHg.

Workup

  1. additionthe addition
  2. stirringstirred
  3. temperatureheated
  4. temperatureunder reflux for 6 h
  5. extractionthis mixture was extracted with chloroform (3×75 ml)
  6. dry with materialThe combined extracts were dried (magnesium sulphate)
  7. customthe solution was then evaporated under reduced pressure
  8. distillationThe resulting brown oil was distilled

Sources & evidence

ORD record
ord-8476652ad48c4c878f85ab5de6916eb7
Source dataset
uspto-grants-1984_02
Patent number
US04431815

Reaction notes

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