Acetonitrile → 5-Benzoyl-2-ethyl-4-methylimidazole

HRID 1462221Notes

Reaction equation

HRID 1462221 reaction equation
C(#N)C.[N:4](=[C:6]([C:15](=O)[CH3:16])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])O.[NH2:18][CH:19]([CH2:24][CH3:25])C(OC)=O.C(C1NC(CC)=NC=1C1C=CC=CC=1)(=O)C>C(O)C.[OH-].[Na+]>[C:7]([C:6]1[NH:4][C:19]([CH2:24][CH3:25])=[N:18][C:15]=1[CH3:16])(=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 1510132-Aminobutyric acid methyl esterHCID 204541395-Acetyl-2-ethyl-4-phenylimidazoleHCID 1784683762-hydroxyimino-1-phenylbutane-1,3-dione

Product 1

HCID 1784376265-Benzoyl-2-ethyl-4-methylimidazoleYield 42%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

An acetonitrile solution (15 ml) of 2-oximino-1-phenyl-1,3-butanedione (1.38 g, 7.22 mmoles) and methyl 2-aminobutyrate (0.85 ml, 7.22 mmol) was refluxed under nitrogen for 26.4 h. After concentrating the cooled reaction mixture, the residue was dissolved in 10 ml of ethanol and 20 ml of 10% aqueous sodium hydroxide. This mixture was refluxed 4.9 h, cooled, then extracted with ethyl acetate. Removal of the solvent in vacuo gave 0.65 g (42% yield) of 5-benzoyl-2-ethyl-4-methylimidazole and 5-acetyl-2-ethyl-4-phenylimidazole (86:14 respectively).

Workup

  1. concentrationAfter concentrating
  2. customthe cooled reaction mixture
  3. temperatureThis mixture was refluxed 4.9 h
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-09375081d0dd468ea6ac6b1b1243ea5d
Source dataset
uspto-grants-1984_07
Patent number
US04459413

Reaction notes

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