Water → 9-Chloro-4-ethyl-8-fluoro-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 548670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548670
[H-].[Na+].[Cl:3][C:4]1[C:5](F)=[C:6]([CH:14]=[CH:15][C:16]=1[F:17])[C:7]([N:9]([CH2:11][CH2:12][OH:13])[CH3:10])=[O:8].O.[CH3:20]N(C=O)C>>[Cl:3][C:4]1[C:5]2[O:13][CH2:12][CH2:11][N:9]([CH2:10][CH3:20])[C:7](=[O:8])[C:6]=2[CH:14]=[CH:15][C:16]=1[F:17]

Komponenten

5

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 576632133-chloro-2,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzamide

Produkt 1

HCID 576631689-Chloro-4-ethyl-8-fluoro-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

Versuchsvorschrift

Sodium hydride (35 mg, 0.913 mmol, 60% dispersion in mineral oil) was added slowly to a solution of 3-chloro-2,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzamide (220 mg, 0.836 mmol) in DMF (4 mL) and the pale yellow solution was stirred at RT for 16 hours. Water was added to the reaction and the mixture was subsequently extracted with DCM (3×30 mL). The combined organic phases were washed with water (3×20 mL) and saturated brine solution then dried (MgSO4), filtered and evaporated to give the desired product as a colourless oil (180 mg). 1H NMR δ (CDCl3): 1.25 (t, 3H), 3.5 (t, 3H), 3.65 (q, 2H), 4.52 (t, 2H), 6.97 (dd, 1H), 7.72 (dd, 1H). m/z 244 (M+H)+, 242 (M−H)−

Aufarbeitung

  1. extractionthe mixture was subsequently extracted with DCM (3×30 mL)
  2. washThe combined organic phases were washed with water (3×20 mL) and saturated brine solution
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b1da9ceae2b845bea9dfa35b29eefafa
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943607B2

Notizen zur Reaktion

Wird geladen…