Trifluoromethanesulfonic acid → 1-Benzoyl-5,5-dimethylimidazolidin-2-one

HRID 2411181Notes

Reaction equation

HRID 2411181 reaction equation
[C:1]([N:9]1[C:13]([CH3:15])([CH3:14])[CH2:12][N:11](CC2C=CC(OC)=CC=2)[C:10]1=[O:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([N:9]1[C:13]([CH3:14])([CH3:15])[CH2:12][NH:11][C:10]1=[O:25])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 712524583-Benzoyl-1-(4-methoxybenzyl)-4,4-dimethylimidazolidin-2-one

Product 1

HCID 712521131-Benzoyl-5,5-dimethylimidazolidin-2-oneYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Benzoyl-1-(4-methoxybenzyl)-4,4-dimethylimidazolidin-2-one (500 mg) described in Preparation Example 57 was dissolved in dichloromethane (5 mL), trifluoromethanesulfonic acid (0.39 mL) was added, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added 5% aqueous sodium hydrogen carbonate solution, the solvent was evaporated, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (146 mg).

Workup

  1. customthe solvent was evaporated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-73656e08363748a8839c80050d0edbc5
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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