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

HRID 1756743Notes

Reaction equation

HRID 1756743 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-6b4a8c05e9294268a9ba6d4002e99276
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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