Water → HCID 76313010, compound

HRID 2081298Notes

Reaction equation

HRID 2081298 reaction equation
[OH:1]/[N:2]=[C:3](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)/[C:4]([NH:6][CH3:7])=[O:5].[C:22](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.O>CC(C)=O>[CH3:22][O:1]/[N:2]=[C:3](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)/[C:4]([NH:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 9795805HCID 9795805, compound

Product 1

HCID 76313010HCID 76313010, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

E-2-hydroxyimino-N-methyl-2-[2-(4-methylphenoxy)phenyl]acetoamide (1.00 g, 0.0035 mole) was dissolved in dried acetone (7 ml), and potassium carbonate (0.63 g, 0.0046 mole) and dimethylsulfate (0.53 g, 0.0042 mole) were added to the mixture, which was reacted at room temperature for 22 hours. After completion of the reaction, water was added to the reaction mixture, which was extracted twice with methylene chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain E-2-methoxyimino-N-methyl-2-[2-(4-methylphenoxy)phenyl] -acetamide as colorless crystals (0.96 g, yield: 92.3%).

Workup

  1. customwas reacted at room temperature for 22 hours
  2. additionwas added to the reaction mixture, which
  3. extractionwas extracted twice with methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-6a21dc624b9a41178cb9bf23d0ce16a3
Source dataset
uspto-grants-1993_02
Patent number
US05183921

Reaction notes

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