N,N-Dimethylaniline → N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamide

HRID 1373735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373735
CN(C)C1C=CC=CC=1.[Br:10][CH2:11][C:12](Br)=[O:13].[CH2:15]([O:22][C:23]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[C:26]([NH2:27])=[C:25]([C:34]([F:37])([F:36])[F:35])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([C:34]([F:36])([F:37])[F:35])[C:26]([NH:27][C:12](=[O:13])[CH2:11][Br:10])=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 210756004-Benzyloxy-2,6-bis(trifluoromethyl)aniline

Produkt 1

HCID 21075603N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamideAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, N,N-dimethylaniline (2.78 mL, 21.9 mmol) and bromoacetyl bromide (1.91 mL, 21.9 mmol) were added dropwise to a solution of 4-benzyloxy-2,6-bis(trifluoromethyl)aniline (4.90 g, 14.6 mmol) in anhydrous toluene (150 mL) under ice cooling. Immediately after the dropwise addition, the mixture was heated under reflux and then stirred for 1 hour. After cooling, the reaction mixture was filtered through Celite and the insoluble matter was washed with toluene. The residue obtained by distilling the filtrate under reduced pressure was purified by chromatography on a silica gel column (developing solvent; hexane:acetone=10:1→6:1→5:1). The crude product thus obtained was recrystallized from hexane-acetone, whereby 4.31 g (yield: 64.7%) of N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamide was obtained as colorless needle-like crystals.

Aufarbeitung

  1. additionImmediately after the dropwise addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite
  6. washthe insoluble matter was washed with toluene
  7. customThe residue obtained
  8. distillationby distilling the filtrate under reduced pressure
  9. customwas purified by chromatography on a silica gel column (developing solvent; hexane:acetone=10:1→6:1→5:1)
  10. customThe crude product thus obtained
  11. customwas recrystallized from hexane-acetone

Quellen und Nachweise

ORD-Eintrag
ord-758d94ad5a20437e9bbeb57198c2ac0d
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163944B2

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