Sodium hydride → 4-benzyl-8-bromo-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one

HRID 886824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 886824
[CH2:1]([N:8]([CH2:19][CH2:20][OH:21])[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=2[O:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 60740299N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

Produkt 1

HCID 685785414-benzyl-8-bromo-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-oneAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide (14.5 g, 41.2 mmol) in N,N-dimethylformamide (200 ml) was added under ice-cooling sodium hydride (60%, 2.14 g, 53.5 mmol), and the mixture was stirred under ice-cooling for 1 hr. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (10.1 g, 73.7%) as an oil.

Aufarbeitung

  1. temperaturecooling for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8b7f1bccb12849bf913402bab94cdfb0
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247403B2

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