Acetohydroxamic Acid → N-phenylmethoxyacetamide

HRID 581105Notes

Reaction equation

HRID 581105 reaction equation
[H-].[Na+].CN(C)C=O.[C:8]([NH:11][OH:12])(=[O:10])[CH3:9].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[CH2:13]([O:12][NH:11][C:8](=[O:10])[CH3:9])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 1990Acetohydroxamic AcidHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 5129184N-phenylmethoxyacetamideYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60% sodium hydride (11.68 g, 0.292 mol) was added to a dimethylformamide solution (200 ml) of acetohydroxamic acid (21.9 g, 0.292 mol) with cooling in an ice bath. After stirring for 1 hour at room temperature, benzylbromide (50 g, 0.292 mol) was added thereto and allowed to react for 24 hours at room temperature. The reaction solution was poured into 500 ml of water, and extracted with ethyl acetate. The organic layer was rinsed with water and dried. After removing the solvent by evaporation, the residue was purified with silica gel chromatography to obtain 31.3 g of N-benzyloxyacetamide (yield: 65%). The proton NMR spectrum of the compound is 1.85 s (3H); 4.89 bs (2H); 7.37 s (5 H); 8.30 bs, 8.81 bs (1H) (solvent: CDCl3).

Workup

  1. temperaturewith cooling in an ice bath
  2. customto react for 24 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was rinsed with water
  5. customdried
  6. customAfter removing the solvent
  7. customby evaporation
  8. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-add983a55a394e76bb629d2827054bd7
Source dataset
uspto-grants-1999_07
Patent number
US05919825

Reaction notes

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