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

HRID 548670Notes

Reaction equation

HRID 548670 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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)−

Workup

  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

Sources & evidence

ORD record
ord-b1da9ceae2b845bea9dfa35b29eefafa
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

Loading…