Sodium hydride → HCID 22058664, Verbindung

HRID 1072800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072800
[Br:1][C:2]1[N:3]=[C:4]([CH3:8])[NH:5][C:6]=1[Br:7].[H-].[Na+].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl>CN(C)C=O>[Br:1][C:2]1[N:3]=[C:4]([CH3:8])[N:5]([CH2:16][O:15][CH2:14][CH2:13][Si:12]([CH3:19])([CH3:18])[CH3:11])[C:6]=1[Br:7]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27733644,5-dibromo-2-methyl-1H-imidazole

Produkt 1

HCID 22058664HCID 22058664, VerbindungAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4,5-Dibromo-2-methylimidazol (4.91 g) was dissolved in N,N-dimethyl-formamide (50 ml) and 60% sodium hydride (901 mg was gradually added under ice-cooling. The mixture was stirred for 1 hr at room temperature, and 2-(trimethylsilyl)ethoxymethyl chloride (3.75 g) was gradually added dropwise under ice-cooling and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and ethyl acetate was added to the residue. The residue was washed with a saturated aqueous sodium hydrogencarbonate solution, and then with brine. The organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give the objective compound (7.6 g) as a colorless oil.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe solvent was evaporated under reduced pressure and ethyl acetate
  5. additionwas added to the residue
  6. washThe residue was washed with a saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customto remove the solvent The residue
  10. customwas purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-1e3965b439924abb9aa85a37bd615e8f
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911469B2

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