Imidazole → 1-(4-Methoxyphenyl)imidazole

HRID 1493968Notes

Reaction equation

HRID 1493968 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 77304-BromoanisoleHCID 11430Potassium Carbonate

Product 1

HCID 823281-(4-Methoxyphenyl)imidazoleYield 50%

Procedure

A mixture of 37.4 g (0.20 mole) of 4-bromoanisole, 170 g (0.25 mole) of imidazole, 26 g (0.2 mole) of potassium carbonate, and 1.2 g of cuprous bromide in 150 ml of N-methylprryolidinone was heated at reflux under a blanket of nitrogen for 4 hr. The mixture filtered and concentrated to remove the solvent. The residue was partioned between dilute sodium hydroxide solution and methylene chloride. After filtration, the organic fraction was chromatographed. The desired fractions were concentrated and the crystalline residue was recrystallized from toluene/cyclohexane to give 17.4 g (50%) of the title compound as white plates, mp 63.0-64.0° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a blanket of nitrogen for 4 hr
  3. filtrationThe mixture filtered
  4. concentrationconcentrated
  5. customto remove the solvent
  6. filtrationAfter filtration
  7. customthe organic fraction was chromatographed
  8. concentrationThe desired fractions were concentrated
  9. customthe crystalline residue was recrystallized from toluene/cyclohexane

Sources & evidence

ORD record
ord-c66284b2d76f466ab3b6f69f02bb41b3
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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