2-Nitroimidazole → 1H-Imidazole, 1-(3-methyl-2-butenyl)-2-nitro-

HRID 634889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634889
C(=O)(O)[O-].[Na+].[CH3:6][C:7]([CH3:11])=[CH:8][CH2:9]Br.[N+:12]([C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)([O-:14])=[O:13]>C(#N)C>[CH3:6][C:7]([CH3:11])=[CH:8][CH2:9][N:16]1[CH:17]=[CH:18][N:19]=[C:15]1[N+:12]([O-:14])=[O:13]

Komponenten

5

Edukt 3

HCID 107012-NitroimidazoleHCID 700922-Butene, 1-bromo-3-methyl-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 113443651H-Imidazole, 1-(3-methyl-2-butenyl)-2-nitro-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Sodium bicarbonate (0.42 g, 50 mmol) and dimethylallyl bromide (3.28 g, 22 mmol) were added to a suspension of 2-nitroimidazole (2.26 g, 20 mmol) in dry acetonitrile (10 mL). The mixture was stirred under reflux for 16 hours. The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was filtered, and dried with anhydrous sodium sulfate. Removal of the solvent gave an oil which was recrystallized from petroleum ether (35-50° C.). Yield 1.83 g, m.p. 48-49° C. 1H NMR (CDCl3) δ 7.24 (s, 1H), 7.22 (s, 1H), 5.46 (m, 1H), 5.1 (d, 2H), 1.91 (s, 3H), and 1.90 (s, 3H).

Aufarbeitung

  1. temperatureunder reflux for 16 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. filtrationThe solution was filtered
  5. dry with materialdried with anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. customgave an oil which
  8. customwas recrystallized from petroleum ether (35-50° C.)

Quellen und Nachweise

ORD-Eintrag
ord-fda3abc7cb88464d97b626f25f155fc3
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184361B2

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