N-bromobutanimide → 1-Benzyl-2-methyl-5-bromo-1H-imidazole

HRID 250743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250743
[Br:1]N1C(=O)CCC1=O.[CH2:9]([N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH3:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[CH2:9]([N:16]1[C:20]([Br:1])=[CH:19][N:18]=[C:17]1[CH3:21])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 836991H-Imidazole, 2-methyl-1-(phenylmethyl)-

Produkt 1

HCID 668687951-Benzyl-2-methyl-5-bromo-1H-imidazoleAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Add N-bromosuccinimide (7.85 g, 44 mmol) to a solution of 1-benzyl-2-methyl-1H-imidazole (8.0 g, 46 mmol) in chloroform (200 mL) and stir for 6 hours. Wash reaction with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, dry over magnesium sulfate, and filter through 2″ pad of silica gel. Concentrate filtrate reduced pressure. Suspend residue in diethyl ether (600 mL), heat to reflux and filter hot Concentrate ether filtrate under reduced pressure to give 9.3 g (37 mmol) of the desired compound as a tan solid.

Aufarbeitung

  1. washWash
  2. customreaction with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter through 2″ pad of silica gel
  5. temperatureSuspend residue in diethyl ether (600 mL), heat
  6. temperatureto reflux
  7. filtrationfilter hot
  8. concentrationConcentrate ether filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f52250e3ee954fa7b57050bbb92284f4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863310B2

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