Ethyl Acetate → N-acetoxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline

HRID 1016577Notes

Reaction equation

HRID 1016577 reaction equation
Cl[CH2:2][C:3]([N:5]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].[C:28]([O-:31])(=[O:30])[CH3:29].[Na+].C(OCC)(=O)C>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:28]([O:31][CH2:2][C:3]([N:5]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4])(=[O:30])[CH3:29]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 18407214HCID 18407214, compound

Product 1

HCID 18407208N-acetoxyacetyl-N-(2-methoxybenzyl)-2-phenoxyanilineYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent

Procedure

In 10 ml of benzene were stirred 1.01 g of N-chloroacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline, 1.30 g of sodium acetate and 170 mg of tetra-n-butyl ammonium bromide at 80° C. for 5 hours. The reaction mixture was poured into ethyl acetate, washed with water and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:3) to give 1.03 g of N-acetoxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline as an oil.

Workup

  1. washwashed with water
  2. dry with materiala saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  3. customAfter removal of the drying agent
  4. filtrationby filtration
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:3)

Sources & evidence

ORD record
ord-8c0ba9defba84a779439d9e1c6edc159
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Reaction notes

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