Diisopropylethylamine → 1-(2-fluoro-4-nitrophenyl)-4-methyl-1H-imidazole

HRID 8155

Reaktionsgleichung

Reaktionsgleichung von HRID 8155
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(N(CC)C(C)C)(C)C.[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F>C(#N)C>[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178418800HCID 178418800, Verbindung

Produkt 1

HCID 218765961-(2-fluoro-4-nitrophenyl)-4-methyl-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Methylimidazole (45.1 g, 0.55 M) and N,N-diisopropylethylamine (161 g, 1.25 M) were dissolved in acetonitrile (800 ml), and 3,4-difluoronitrobenzene (79.5 g, 0.5 M) added. The mixture was stirred and heated to reflux under nitrogen for 24 hours. Solvent was evaporated, the residue dissolved in ethyl acetate (800 ml), washed with water (400 ml), brine (200 ml), and dried (magnesium sulfate). The residue was dissolved in toluene (250 ml), treated with charcoal, filtered, and diluted with hot cyclohexane (75 ml) to crystallise 3-fluoro-4-(4-methylimidazol-1-yl)nitrobenzene (64.7 g).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 24 hours
  3. customSolvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate (800 ml)
  5. washwashed with water (400 ml), brine (200 ml)
  6. dry with materialdried (magnesium sulfate)
  7. dissolutionThe residue was dissolved in toluene (250 ml)
  8. additiontreated with charcoal
  9. filtrationfiltered
  10. additiondiluted with hot cyclohexane (75 ml)
  11. customto crystallise 3-fluoro-4-(4-methylimidazol-1-yl)nitrobenzene (64.7 g)

Quellen und Nachweise

ORD-Eintrag
ord-dc7b9a5830914572958c7fec79e92c2d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087629B2

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