Ethyl Acetate → 3-Benzyl-2,5-dioxo-4,4-dimethylimidazolidine

HRID 1597415

Reaction equation

HRID 1597415 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:14])([CH3:13])[C:11](=[O:15])[N:10](CC2C=CC(OC)=CC=2)[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[Ce].[NH4+].C(OCC)(=O)C>C(#N)C.O>[CH2:1]([N:8]1[C:12]([CH3:14])([CH3:13])[C:11](=[O:15])[NH:10][C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 217000233-Benzyl-1-(4'-methoxybenzyl)-2,5-dioxo-4,4-dimethylimidazolidineHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 46019883-Benzyl-2,5-dioxo-4,4-dimethylimidazolidineYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-benzyl-1-(4′-methoxybenzyl)-2,5-dioxo-4,4-dimethylimidazolidine (3.9 g, 11.54 mmol) in acetonitrile (100 mL) was treated with a solution of ammonium cerium nitrate (31 g, 57.7 mmol) in 65 mL of water, stirred at 25° C. for 15 minute, then diluted the reaction with ethyl acetate and partitioned between ethyl acetate and brine. The organic layer was dried, filtered, and concentrated. Purification by recrystalization with ethyl acetate/hexane provided 1.58 g (7.25 mmol, 63%) of title compound as white solid. MS (DCI/NH3) m/e 236 (M+NH4)+.

Workup

  1. additiondiluted
  2. custompartitioned between ethyl acetate and brine
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. customby recrystalization with ethyl acetate/hexane

Sources & evidence

ORD record
ord-f9b1043869084f6a82e62629f8946f86
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Linked notes

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