Water → 1-Phenethyl-4-phenyl-imidazole

HRID 1773859Notes

Reaction equation

HRID 1773859 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:14](OS(C)(=O)=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:14]([N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9]1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 146679Methanesulfonic acid, 2-phenylethyl esterHCID 178418822HCID 178418822, compound

Product 1

HCID 572929641-Phenethyl-4-phenyl-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-phenyl-1H-imidazole (1 g, 8.75 mmoles) in DMF (8 mL) is added NaH 60% dispersion in mineral oil (455 mg, 11 mmoles). The reaction mixture is stirred at room temperature for 1 hour, then methanesulfonic acid phenethyl ester (example 4D) (1.84 g, 9.12 mmoles) is added. The reaction mixture is then heated at 60° C. for 2 hours. Water is added, and the aqueous phase is extracted three times with AcOEt. The organic phase is washed with water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH) (100:0) then (98:2) to give 1-phenethyl-4-phenyl-imidazole.

Workup

  1. temperatureThe reaction mixture is then heated at 60° C. for 2 hours
  2. extractionthe aqueous phase is extracted three times with AcOEt
  3. washThe organic phase is washed with water, brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-8ce6ed6a32b14a03822ba22b74aa1566
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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