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

HRID 548664Notes

Reaction equation

HRID 548664 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>CN(C=O)C>[Cl:3][C:4]1[C:5]2[O:13][CH2:12][CH2:11][N:9]([CH3:10])[C:7](=[O:8])[C:6]=2[CH:14]=[CH:15][C:16]=1[F:17]

Participants

5

Reactant 3

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

Product 1

HCID 576632269-chloro-8-fluoro-4-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-oneYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (28 mg, 0.723 mmol, 60% dispersion in mineral oil) was added slowly to a solution of 3-chloro-2,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzamide (180 mg, 0.723 mmol) in DMF (4 mL) and the reaction stirred at room temperature 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 (5×25 mL) and saturated brine solution then dried (MgSO4), filtered and evaporated to give the desired product as an oil (140 mg). 1H NMR δ (CDCl3): 3.21 (s, 3H), 3.54 (t, 2H), 4.52 (t, 2H), 6.97 (dd, 1H), 7.72 (dd, 1H). m/z 230 (M+H)+

Workup

  1. extractionthe mixture was subsequently extracted with DCM (3×30 mL)
  2. washThe combined organic phases were washed with water (5×25 mL) and saturated brine solution
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-960105b779dd409f8b309757839a931d
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

Loading…