Sodium hydride → HCID 19808453, Verbindung

HRID 373776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373776
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH:6]=[N:5]2.[H-].[Na+].Br[CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CN(C=O)C>[CH2:21]([O:20][C:18]([CH2:17][N:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[C:11]([Cl:12])[CH:10]=2)[N:5]=[CH:6][C:7]1=[O:13])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 144236366,7-Dichloroquinoxalin-2(1H)-one

Produkt 1

HCID 19808453HCID 19808453, VerbindungAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere 6,7-dichloroquinoxalin-2(1H)-one (10.0 g, 46.5 mmol) (Liebigs Ann. Chem, (1982), 754) was suspended in 135 ml of dry DMF and sodium hydride (2.23 g, 55.8 mmol (60% mineral oil dispersion)) was added. After stirring for 2 h, benzyl bromoacetate (9.18 ml, 58.6 mmol) was added and the mixture was stirred for 3.5 h. The reaction mixture was poured onto 300 g of crushed ice and the precipitate was filtered off, washed with water and dried. The product was triturated with ether (500 ml), the precipitate filtered off, washed with ether and dried to afford 13.3 g of 1-benzyloxycarbonylmethyl-6,7-dichloroquinoxaline-2(1H)-one. 1H-NMR (DMSO-d6):δ5.18(s, 2H), 5.23(s, 1H), 8.18(s, 1H), 8.38(s, 1H).

Aufarbeitung

  1. stirringthe mixture was stirred for 3.5 h
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customThe product was triturated with ether (500 ml)
  6. filtrationthe precipitate filtered off
  7. washwashed with ether
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cdfd555fc542460d9d37b6a69adb8061
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166155

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