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

HRID 23561

Reaktionsgleichung

Reaktionsgleichung von HRID 23561
[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]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10006HydantoinHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a177bfd3d8ad4100ac66ba9e9201f412
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852744B2

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