Imidazole → 1-(4-Biphenylyl)-2-(imidazol-1-yl)-1-phenyl-ethanol

HRID 1633375Notes

Reaction equation

HRID 1633375 reaction equation
C[O-].[Na+].[NH:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[C:9]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:14]=[CH:13][C:12]([C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:18])[CH2:16]Cl)=[CH:11][CH:10]=1>CO.CN(C)C=O>[C:9]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:10]=[CH:11][C:12]([C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:18])[CH2:16][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 10942334Sodium MethoxideHCID 204410081-(4-Biphenylyl)-2-chloro-1-phenyl-ethanol

Product 1

HCID 130136401-(4-Biphenylyl)-2-(imidazol-1-yl)-1-phenyl-ethanolYield 21%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

2.45 g (0.045 mol) of sodium methylate are dissolved in 20 ml of methanol, and 5.25 g (0.077 mol) of imidazole are added. A solution of 11.1 g (0.077 mol) of 1-(4-biphenylyl)-2-chloro-1-phenyl-ethanol in 50 ml of dimethylformamide is added dropwise to this mixture and the reaction mixture is heated under reflux for 16 hours. Thereafter, it is poured onto water and the crystals which form are extracted with hot acetonitrile. 3.2 g (21% of theory) of 1-(4-biphenylyl)-2-(imidazol-1-yl)-1-phenyl-ethanol of melting point 224° C. are obtained.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 hours
  3. additionThereafter, it is poured onto water
  4. extractionthe crystals which form are extracted with hot acetonitrile

Sources & evidence

ORD record
ord-0cda5629e4124576993cd3cf3808bbe8
Source dataset
uspto-grants-1984_10
Patent number
US04480114

Reaction notes

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