Water → Phenylmethyl 2-(2,5-dioxoimidazolidinyl)acetate

HRID 23561

Reaction equation

HRID 23561 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].O>CN(C=O)C>[O:3]=[C:2]1[NH:1][CH2:7][C:5](=[O:6])[N:4]1[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 10006HydantoinHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 22574607Phenylmethyl 2-(2,5-dioxoimidazolidinyl)acetateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of hydantoin (10.0 g, 0.10 mol) in DMF (100 ml) at 60° C. were added potassium carbonate (20.7 g, 0.15 mol) and benzyl bromoacetate (18.9 ml, 0.12 mol). After stirring the mixture at 60° C. overnight, the reaction mixture was poured into water (250 ml) and the mixture was extracted with ethyl acetate. The organic phase was washed with 5% aqueous citric acid solution and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The crystalline residue was washed with diethyl ether, and dried to give phenylmethyl 2-(2,5-dioxoimidazolidinyl)acetate (14.9 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with 5% aqueous citric acid solution and brine
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. washThe crystalline residue was washed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-a177bfd3d8ad4100ac66ba9e9201f412
Source dataset
uspto-grants-2005_02
Patent number
US06852744B2

Linked notes

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