Water → 1-Methyl-5-phenyl-1H-imidazole

HRID 2231254Notes

Reaction equation

HRID 2231254 reaction equation
C([N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]=[CH:5]1)(=O)C.[CH3:15]I.O>C(#N)C>[CH3:15][N:6]1[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:8][N:4]=[CH:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 108214021-Acetyl-4-phenylimidazole

Product 1

HCID 37463431-Methyl-5-phenyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2.88 g of 1-acetyl-4-phenylimidazole in 50 ml of acetonitrile was added 5.8 ml of methyl iodide and the reaction mixture sealed in a flask over a weekend. The reaction mixture was poured into water and then decanted from insoluble oil. The pH of the decanted solution was adjusted to 9 with sodium carbonate and the solution extracted with chloroform. The extracts were combined, dried over magnesium sulfate and concentrated to give 1.02 g of crude product which was chromatographed on 50 g of silica gel using 30% ethyl acetate in chloroform as the eluent, 640 mg.

Workup

  1. customthe reaction mixture sealed in a flask over a weekend
  2. customdecanted from insoluble oil
  3. extractionthe solution extracted with chloroform
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-13d75eb2c2994c5dbcb6047becab4022
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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