Hydroxylamine, sulfate (1:1) → (2E)-2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-hydroxyimino-N-methylacetamide

HRID 1779719Notes

Reaction equation

HRID 1779719 reaction equation
[CH3:1][NH:2][C:3](=[O:22])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21])=O.S(O)(O)(=O)=O.[NH2:28][OH:29]>CO>[CH3:1][NH:2][C:3](=[O:22])/[C:4](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21])=[N:28]/[OH:29]

Participants

4

Reactant 2

HCID 159255Hydroxylamine, sulfate (1:1)HCID 110877922-[2-(2,5-dimethylphenoxymethyl)phenyl]-N-methyl-2-oxoacetamide

Product 1

HCID 15790180(2E)-2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-hydroxyimino-N-methylacetamideYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-oxoacetamide (11.89 g, 0.04 mol) was suspended in methanol (40 ml). Hydroxylamine sulfate (4.92 g, 0.06 mol) was added, and the mixture was refluxed for 8 hours. After completion of the reaction, methanol was evaporated under reduced pressure. The resulting residue (E/Z=46/54) was dissolved in methylene chloride (80 ml), conc. hydrochloric acid (20 ml) was added, and the mixture was stirred at room temperature for 15 hours. Water (50 ml) and toluene (80 ml) were added, and the mixture was stirred at room temperature for 5 minutes. Then the resulting crystals were separated by filtration, washed with water (50 ml) and toluene (50 ml) and dried to give (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-hydroxyiminoacetamide (11.32 g, Yield: 90.6%, E/Z=99/1).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customwas evaporated under reduced pressure
  3. dissolutionThe resulting residue (E/Z=46/54) was dissolved in methylene chloride (80 ml)
  4. additionconc. hydrochloric acid (20 ml) was added
  5. additionWater (50 ml) and toluene (80 ml) were added
  6. stirringthe mixture was stirred at room temperature for 5 minutes
  7. customThen the resulting crystals were separated by filtration
  8. washwashed with water (50 ml) and toluene (50 ml)
  9. customdried

Sources & evidence

ORD record
ord-6b33f9706847465dbc276de1f94122fc
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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