Water → HCID 18670149, Verbindung

HRID 1059388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059388
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][NH:9][C:10](=[O:12])[CH3:11].[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl.O>CN(C)C=O.C(OCC)(=O)C>[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][NH:9][C:10](=[O:12])[CH3:11]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 18670192N-[(1H-imidazol-2-yl)methyl]acetamide

Produkt 1

HCID 18670149HCID 18670149, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under ice-cooling, 0.08 g of sodium hydride (60% oily) was added to a solution of 0.31 g of N-(imidazol-2-ylmethyl)acetamide in N,N-dimethylformamide (10 ml). After stirring for 15 minutes, a solution of 0.35 ml of 2-(trimethylsilyl)ethoxymethyl chloride in N,N-dimethylformamide (1 ml) was dropped thereinto and the resulting mixture was stirred at room temperature for additional 16 hours. Then the reaction mixture was distributed into water and ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.16 g of the title compound as a colorless oily substance.

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. stirringthe resulting mixture was stirred at room temperature for additional 16 hours
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentrating under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-c14974c2712e4042a06800136c02682d
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518423B1

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