Water → 4-benzyl-8,9-difluoro-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 548668Notes

Reaction equation

HRID 548668 reaction equation
[H-].[Na+].[CH2:3]([N:10]([CH2:22][CH2:23][OH:24])[C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[C:13]=1F)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CN(C=O)C>[CH2:3]([N:10]1[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[C:13]=2[O:24][CH2:23][CH2:22]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 57663176N-benzyl-2,3,4-trifluoro-N-(2-hydroxyethyl)benzamide

Product 1

HCID 576631824-benzyl-8,9-difluoro-3,4-dihydro-1,4-benzoxazepin-5(2H)-oneYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (25 mg, 0.615 mmol, 60% dispersion in mineral oil) was added slowly to a solution of N-benzyl-2,3,4-trifluoro-N-(2-hydroxyethyl)benzamide (190 mg, 0.615 mmol) in DMF (3 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 (4×30 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 (130 mg). 1H NMR δ (CDCl3): 3.5 (t, 2H), 4.3 (t, 2H), 4.8 (s, 2H), 6.92 (dd, 1H), 7.3-7.4 (m, 5H), 7.7 (m, 1H)

Workup

  1. extractionthe mixture was subsequently extracted with DCM (4×30 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-d5b39d49d35141ab89520e1c63a52848
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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