Cesium carbonate → 4-Benzyl-1-phenethyl-imidazole

HRID 1773889Notes

Reaction equation

HRID 1773889 reaction equation
[CH2:1]([C:8]1[N:9]=[CH:10][NH:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:25](OS(C)(=O)=O)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C>[CH2:1]([C:8]1[N:9]=[CH:10][N:11]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 146679Methanesulfonic acid, 2-phenylethyl esterHCID 178420208HCID 178420208, compound

Product 1

HCID 233683114-Benzyl-1-phenethyl-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-benzyl-1H-imidazole (example 110C) (1.23 g, 7.78 mmoles) in ACN (20 mL) are added K2CO3 (1.29 g, 9.34 mmoles), Cs2CO3 (253 mg, 0.778 mmole) and methanesulfonic acid phenethyl ester (example 4D) (1.86 g, 9.34 mmole). The reaction mixture is heated at reflux overnight, then cooled to room temperature, filtered, cake washed with ACN and filtrate concentrated under reduced pressure. The residue is purified by silica gel chromatography using (toluene:acetone) (90:10) to give 4-benzyl-1-phenethyl-imidazole.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. washcake washed with ACN and filtrate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f75272429768482ca00e7f4296cd9b20
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

Loading…