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

HRID 1597415

Reaktionsgleichung

Reaktionsgleichung von HRID 1597415
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f9b1043869084f6a82e62629f8946f86
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294573B1

Verknüpfte Notizen

Wird geladen…