Water → 4-Iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole

HRID 735364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735364
[I:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl.O>CN(C=O)C>[I:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 210995124-Iodo-1H-benzimidazole

Produkt 1

HCID 689001214-Iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazoleAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirring solution of 4-iodo-1H-benzimidazole (1.00 g, 4.1 mmol) in DMF (12 mL) was added sodium hydride (180 mg of a 60% dispersion in mineral oil; 4.5 mmol), and the resulting mixture was stirred at room temperature under nitrogen for 50 minutes. 2-(Trimethylsilyl)ethoxymethyl chloride (870 μL, 4.92 mmol) was added dropwise over 5 minutes at room temperature, then the mixture was stirred overnight. Water (50 mL) was added, and the mixture was washed with ethyl acetate (3×25 mL). The combined organic layers were washed with water (2×30 mL), then with saturated sodium chloride solution (30 mL), then dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 0 to 20% ethyl acetate in dichloromethane, affording the product as a white solid (1.20 g, 78%). 1H NMR (400 MHz, CDCl3): δ 8.05 (1H, s), 7.74 (1H, dd, J=0.6, 7.5 Hz), 7.52 (1H, t, J=4.2 Hz), 7.09 (1H, t, J=7.9 Hz), 5.51 (2H, s), 3.50 (2H, t, J=8.2 Hz), 0.90 (2H, dd, J=8.3, 16.4 Hz), −0.05 (9H, s); m/z (ES+) 375 [MH+].

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. washthe mixture was washed with ethyl acetate (3×25 mL)
  3. washThe combined organic layers were washed with water (2×30 mL)
  4. dry with materialwith saturated sodium chloride solution (30 mL), then dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel
  7. washeluting with 0 to 20% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-ada2dd3fadaf4181a14cc39c27c97f3d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592456B2

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