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

HRID 1633374

Reaction equation

HRID 1633374 reaction equation
[H-].[Na+].[I-].C[S+](C)(C)=O.[H][H].[C:11]1([C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:31][O-].[Na+].[NH:34]1[CH:38]=[CH:37][N:36]=[CH:35]1>CS(C)=O.CN(C)C=O.CO.O>[C:22]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:20][C:19]([C:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([OH:18])[CH2:31][N:34]2[CH:38]=[CH:37][N:36]=[CH:35]2)=[CH:24][CH:23]=1

Participants

11

Reactant 6

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 750404-BenzoylbiphenylHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 130136401-(4-Biphenylyl)-2-(imidazol-1-yl)-1-phenyl-ethanolYield 83.5%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

120 ml of dimethylsulphoxide are added to 3.6 g (0.12 mol) of 80% strength sodium hydride and 26.4 g (0.12 mol) of trimethyloxosulphonium iodide in the course of 20 minutes. When the evolution of hydrogen has ended, a solution of 25.8 g (0.1 mol) of 4-biphenylyl phenyl ketone in 150 ml of dimethylsulphoxide is added dropwise and the mixture is subsequently stirred at 60° C. for 2 hours. 300 ml of water are added dropwise to the reaction mixture obtained. The resulting oil is separated off from the aqueous phase and dissolved in chloroform and the solution is washed with water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The crude 2-(4-biphenylyl)-2-phenyl-oxirane thus obtained is dissolved in 150 ml of dimethylformamide. This solution is added dropwise to a mixture of 7 g (0.13 mol) of sodium methylate, 40 ml of methanol and 15 g (0.22 mol) of imidazole. The reaction mixture is heated to 80° C. for 4 hours. Thereafter, it is concentrated in vacuo, the residue is poured onto water and the crystals which form are filtered off and washed with acetonitrile. 26.7 g (83.5% of theory) of 1-(4-biphenylyl)-2-(imidazol-1-yl)-1-phenyl-ethanol of melting point 224° C. are obtained.

Workup

  1. customobtained
  2. customThe resulting oil is separated off from the aqueous phase
  3. dissolutiondissolved in chloroform
  4. washthe solution is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. distillationby distilling off the solvent in vacuo
  8. customThe crude 2-(4-biphenylyl)-2-phenyl-oxirane thus obtained
  9. temperatureThe reaction mixture is heated to 80° C. for 4 hours
  10. concentrationThereafter, it is concentrated in vacuo
  11. additionthe residue is poured onto water
  12. filtrationthe crystals which form are filtered off
  13. washwashed with acetonitrile

Sources & evidence

ORD record
ord-0e729da6b3eb46748dcdf78f9ce6e484
Source dataset
uspto-grants-1984_10
Patent number
US04480114

Linked notes

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