Dinitrofluorobenzene → 1-(2,4-Dinitrophenyl)-2-(chloromethyl)imidazole

HRID 1587485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587485
Cl.[Cl:2][CH2:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1F)([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[CH2:3][Cl:2])([O-:11])=[O:10]

Komponenten

5

Edukt 3

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 27609292-(Chloromethyl)-1H-imidazole hydrochloride

Produkt 1

HCID 156371921-(2,4-Dinitrophenyl)-2-(chloromethyl)imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-(Chloromethyl)imidazole hydrochloride (920 mg) was dissolved in 5 ml of acetonitrile. To this solution was added 830 μL of 2,4-dinitrofluorobenzene and 2.5 g of potassium carbonate. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried (sodium sulfate) and concentrated. The crude reaction product was purified by flash silica gel chromatography (1:1 ethyl acetate-hexane elution) to give 710 mg of the title compound as a yellow solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe crude reaction product
  6. customwas purified by flash silica gel chromatography (1:1 ethyl acetate-hexane elution)

Quellen und Nachweise

ORD-Eintrag
ord-6ad5cbefef4a4d379546e094972756db
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05218115

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