Imidazole → Acetophenone, 2-(imidazol-1-yl)-

HRID 1834032Notes

Reaction equation

HRID 1834032 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1>CO>[N:11]1([CH2:1][C:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 6259Phenacyl bromide

Product 1

HCID 32235Acetophenone, 2-(imidazol-1-yl)-Yield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenacyl bromide (0.05 mol) and imidazole (0.02 mol) were stirred in methanol (50 ml) at 0° for 3 hours. The methanol was removed in vacuo and the residue taken up in methylene chloride (300 ml), washed with water (3 × 100 ml), and dried (anhydrous sodium sulphate). Removal of the solvent left a solid residue which on recrystallisation from ethyl acetate gave 2-(imidazol-1-yl)-acetophenone (60%) as light brown needles, m.p. 112°-113°.

Workup

  1. customThe methanol was removed in vacuo
  2. washwashed with water (3 × 100 ml)
  3. dry with materialdried (anhydrous sodium sulphate)
  4. customRemoval of the solvent
  5. waitleft a solid residue which
  6. customon recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-2273bb47c55d47d393c4e1076b725893
Source dataset
uspto-grants-1978_01
Patent number
US04067989

Reaction notes

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