Ammonium Acetate → 5-Benzyl-4-isopropyl-2-methylimidazole

HRID 1728337Notes

Reaction equation

HRID 1728337 reaction equation
[C:1]([NH:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6](=O)[CH:7]([CH3:9])[CH3:8])(=O)[CH3:2].C([O-])(=O)C.[NH4+:22]>C(O)(=O)C>[CH2:11]([C:5]1[NH:4][C:1]([CH3:2])=[N:22][C:6]=1[CH:7]([CH3:9])[CH3:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 190029664-Acetylamino-2-methyl-5-phenyl-3-pentanone

Product 1

HCID 190029815-Benzyl-4-isopropyl-2-methylimidazoleYield 0.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.00 g of 4-acetylamino-2-methyl-5-phenyl-3-pentanone (4.29 mmol) in 20 ml of acetic acid is added 5.00 g of ammonium acetate (64.9 mmol), and the resultant mixture is heated under reflux. One hour later, the reaction mixture is concentrated in vacuo, neutralized with aqueous sodium bicarbonate and extracted with ethyl acetate. The extract is washed with saturated brine, dried over sodium sulfate, filtered and the filtrate is concentrated. The crude product is recrystallized from ether/n-hexane to give 0.90 mg of the objective 5-benzyl-4-isopropyl-2-methylimidazole 6. Yield, 97.5%.

Workup

  1. temperatureunder reflux
  2. concentrationOne hour later, the reaction mixture is concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated
  8. customThe crude product is recrystallized from ether/n-hexane

Sources & evidence

ORD record
ord-a74d0aafbbe14ecf9e4b0490286984e7
Source dataset
uspto-grants-1994_07
Patent number
US05326780

Reaction notes

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