Ethyl Acetate → 4-(5,5-Dimethyl-3-naphthylcarbonyl-2,4-dioxoimidazolidinylmethyl)benzonitrile

HRID 896600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896600
[CH3:1][C:2]1([CH3:21])[NH:6][C:5](=[O:7])[N:4]([C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[O:9])[C:3]1=[O:20].[H-].[Na+].[C:24]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)#[N:25].C(OCC)(=O)C>CN(C=O)C>[CH3:1][C:2]1([CH3:21])[N:6]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([C:24]#[N:25])=[CH:27][CH:28]=2)[C:5](=[O:7])[N:4]([C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[O:9])[C:3]1=[O:20]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 121120155,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione

Produkt 1

HCID 697325524-(5,5-Dimethyl-3-naphthylcarbonyl-2,4-dioxoimidazolidinylmethyl)benzonitrileAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5,5-Dimethyl-3-naphthylcarbonylimidazolidine -2,4-dione (35 mg) was dissolved in DMF (0.4 mL) and sodium hydride (60%, in oil) (5 mg) was added. Then, 4-cyanobenzyl bromide (25 mg) was added, and the mixture was stirred at room temperature overnight. Ethyl acetate (9.5 mL) was added to the reaction solution, separated out white precipitates were filtered, and the filtrate was concentrated and purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 24 mg of white crystals.

Aufarbeitung

  1. customseparated out white
  2. customprecipitates
  3. filtrationwere filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by silica gel chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-7c94c1868c964b84a52f8cdbd8635c93
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919365B2

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