3-Benzyl-1-(4'-methoxybenzyl)-2,5-dioxo-4,4-dimethylimidazolidine → 3-Benzyl-2,5-dioxo-4,4-dimethylimidazolidine

HRID 1978026

Reaction equation

HRID 1978026 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(#N)C.O.C(OCC)(=O)C>[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 2

HCID 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 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

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 minutes, then diluted 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 the desired product as white solid.

Workup

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

Sources & evidence

ORD record
ord-fae5a3e119b24dd999adacb62565b9ba
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Linked notes

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