3-Benzoyl-1-(4-methoxybenzyl)-4-methylimidazolidin-2-one → 1-Benzoyl-5-methylimidazolidin-2-one

HRID 2411179Notes

Reaction equation

HRID 2411179 reaction equation
[C:1]([N:9]1[CH:13]([CH3:14])[CH2:12][N:11](CC2C=CC(OC)=CC=2)[C:10]1=[O:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[C:1]([N:9]1[CH:13]([CH3:14])[CH2:12][NH:11][C:10]1=[O:24])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 712521503-Benzoyl-1-(4-methoxybenzyl)-4-methylimidazolidin-2-one

Product 1

HCID 712527551-Benzoyl-5-methylimidazolidin-2-oneYield 97.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-Benzoyl-1-(4-methoxybenzyl)-4-methylimidazolidin-2-one (220 mg) described in Preparation Example 55 was dissolved in trifluoroacetic acid (2 mL), and the mixture was stirred for 4 hr under heated reflux. The solvent was evaporated from the reaction mixture, 5% aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (135 mg).

Workup

  1. temperatureunder heated
  2. temperaturereflux
  3. customThe solvent was evaporated from the reaction mixture, 5% aqueous sodium hydrogen carbonate solution
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-b112b17ff10c407087f9098365c5bcda
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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