Sodium hydride → Ethyl 2-(4-nitro-1H-imidazole-1-yl)octanoate

HRID 375112

Reaktionsgleichung

Reaktionsgleichung von HRID 375112
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CN(C=O)C>[N+:1]([C:4]1[N:5]=[CH:6][N:7]([CH:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 95580Ethyl 2-bromooctanoateHCID 178526856HCID 178526856, Verbindung

Produkt 1

HCID 10062368Ethyl 2-(4-nitro-1H-imidazole-1-yl)octanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Nitroimidazole (0.29 moles, 32.9 g in 30 ml DMF was treated portionwise with sodium hydride (0.29 moles, 11.6 g. 60% in mineral oil) and stirred for 45 minutes. Ethyl 2-bromooctanoate (0.29 moles, 73.1 g) was added dropwise over 1 hour. The reaction was stirred overnight at room temperature, poured onto ice water, and extracted with ethyl acetate. The organic phase was washed with brine, dried and concentrated to yield 91 g of ethyl 2-(4-nitro-1H-imidazol-1-yl)octanoate. (MS)

Aufarbeitung

  1. stirringThe reaction was stirred overnight at room temperature
  2. additionpoured onto ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dbd66e6369174d8aa63f577dbde71f8d
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484780

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