Imidazole → 1-(4-Methoxyphenyl)imidazole

HRID 327652Notes

Reaction equation

HRID 327652 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+]>CN1CCCC1=O>[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

5

Reactant 3

HCID 795ImidazoleHCID 77304-BromoanisoleHCID 11430Potassium Carbonate

Product 1

HCID 823281-(4-Methoxyphenyl)imidazoleYield 50%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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-methylpyrrolidinone was heated at reflux under a blanket of nitrogen for 4 hr. The mixture was filtered and concentrated to remove the solvent. The residue was partitioned 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 was filtered
  4. concentrationconcentrated
  5. customto remove the solvent
  6. customThe residue was partitioned between dilute sodium hydroxide solution and methylene chloride
  7. filtrationAfter filtration
  8. customthe organic fraction was chromatographed
  9. concentrationThe desired fractions were concentrated
  10. customthe crystalline residue was recrystallized from toluene/cyclohexane

Sources & evidence

ORD record
ord-e738ebc4e92c4f76b9068fb9e90c878b
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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