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

HRID 2411178Notes

Reaction equation

HRID 2411178 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH2:12][CH:11]([CH3:13])[NH:10][C:9]2=[O:14])=[CH:5][CH:4]=1.[H-].[Na+].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>CN(C)C=O>[C:19]([N:10]1[CH:11]([CH3:13])[CH2:12][N:8]([CH2:7][C:6]2[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]1=[O:14])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 712520041-(4-Methoxybenzyl)-4-methylimidazolidin-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen stream, 1-(4-methoxybenzyl)-4-methylimidazolidin-2-one (300 mg) described in Preparation Example 52 was dissolved in N,N-dimethylformamide (3 mL), sodium hydride (60 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 30 min. Then, benzoyl chloride (0.17 mL) was added under ice-cooling, and the mixture was stirred at the same temperature for 30 min and at room temperature for 2 hr. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 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 (220 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at the same temperature for 30 min and at room temperature for 2 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water, 5% aqueous sodium hydrogen carbonate solution and saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-a79a617e88ad4aa98d42a4028b86d6b6
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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