Imidazole → 1-(4-Nitrophenyl)-1H-imidazole

HRID 1419775

Reaktionsgleichung

Reaktionsgleichung von HRID 1419775
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.O>CN(C=O)C>[N:1]1([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride

Produkt 1

HCID 1231551-(4-Nitrophenyl)-1H-imidazoleAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred solution of imidazole (34.1 g, 0.50 mol) in DMF (300 ml) under Ar, was added portionwise, over 23 minutes, 60% NaH in oil (20.02 g, 0.50 mol). The mixture was then stirred at room temperature for 18 minutes before adding dropwise, over 40 minutes, a solution of 1-fluoro-4-nitrobenzene (70.62 g, 0.50 mol) in DMF (60 ml). The mixture was then stirred at room temperature overnight. Water (600 ml) was then added and the solid was filtered off, washed with water, then stirred in boiling ethyl acetate (400 ml), allowed to cool and filtered, washing the solid with more ethyl acetate (50 ml), then petroleum ether (250 ml). The filtrate, now containing more solid, was refiltered and washed with petroleum ether. The combined solids were dried in a vacuum desiccator overnight to give 90.14 g (95%) of the title compound as a yellow solid. δH (360 MHz, DMSO-d6) 7.19 (1H, t, J=1.1 Hz), 7.97-8.03 (3H, m), 8.38 (2H, d, J=9.2 Hz), 8.52 (1H, t).

Aufarbeitung

  1. additionbefore adding dropwise, over 40 minutes
  2. stirringThe mixture was then stirred at room temperature overnight
  3. filtrationthe solid was filtered off
  4. washwashed with water
  5. stirringstirred
  6. temperatureto cool
  7. filtrationfiltered
  8. washwashing the solid with more ethyl acetate (50 ml)
  9. additionThe filtrate, now containing more solid
  10. washwashed with petroleum ether
  11. customThe combined solids were dried in a vacuum desiccator overnight

Quellen und Nachweise

ORD-Eintrag
ord-3244dd21988a4298beb37cc9f42fbe03
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889008

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