Potassium Carbonate → 5-Methyl-1-phenethyl-4-phenyl-imidazole

HRID 1773888Notes

Reaction equation

HRID 1773888 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](OS(C)(=O)=O)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[CH3:1][C:2]1[N:6]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:5]=[N:4][C:3]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1.[CH3:1][C:2]1[N:6]=[CH:5][N:4]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 146679Methanesulfonic acid, 2-phenylethyl esterHCID 8170055-methyl-4-phenyl-1H-imidazole

Product 2

HCID 867039665-Methyl-1-phenethyl-4-phenyl-imidazoleHCID 867039674-Methyl-1-phenethyl-5-phenyl-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-methyl-4-phenyl-1H-imidazole (example 103D) (1.02 g, 6.44 mmoles) in ACN (20 mL) are added K2CO3 (1.07 g, 7.72 mmoles) and methanesulfonic acid phenethyl ester (example 4D). The reaction mixture is heated at reflux overnight, then cooled to room temperature, filtered, cake washed with ACN and solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (toluene:acetone) (90:10) as eluent to give 5-methyl-1-phenethyl-4-phenyl-imidazole and 4-methyl-1-phenethyl-5-phenyl-imidazole.

Workup

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

Sources & evidence

ORD record
ord-81048ad271874f8e9be78288c3725ad9
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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