Potassium Carbonate → 4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-fluorophenyl)-1H-imidazole

HRID 1599429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599429
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:21]([O:20][C:18]([C:17]1[N:16]=[CH:15][N:14]([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[C:13]=1[CH3:12])=[O:19])[CH3:22]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 178470400HCID 178470400, Verbindung

Produkt 1

HCID 189281094-ethoxycarbonyl-5-methyl-1-(2-nitro-5-fluorophenyl)-1H-imidazoleAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 2,4-difluoronitrobenzene (36.6 g, 230 mmol), ethyl 4-methyl-5-imidazolecarboxylate (35.6 g, 231 mmol), potassium carbonate (36.5 g, 264.4 mmol) and acetonitrile (250 ml) was stirred at 25° C. for 96 h. The reaction mixture was filtered and the solvent removed under reduced pressure. The residue was submitted to flash chromatography on silica gel 60 eluting with toluene graduated to toluene/ethyl acetate (1:1) to give 30.5 g (65%) of 4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-fluorophenyl)-1H-imidazole.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-698d7379085c4a26a2d83f8162df760c
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05741785

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