Water → 3-(4-methylbenzyloxyimino)-2-methoxyimino-N,N-dimethylbutyramide

HRID 1069195

Reaction equation

HRID 1069195 reaction equation
[OH:1][N:2]=[C:3]([CH3:13])[C:4](=[N:10][O:11][CH3:12])[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[CH3:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:1][N:2]=[C:3]([CH3:13])[C:4](=[N:10][O:11][CH3:12])[C:5]([N:7]([CH3:8])[CH3:9])=[O:6])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77224-Methylbenzyl chlorideHCID 11430Potassium CarbonateHCID 1361176603-hydroxyimino-2-methoxyimino-N,N-dimethylbutyramide

Product 1

HCID 536799603-(4-methylbenzyloxyimino)-2-methoxyimino-N,N-dimethylbutyramideYield 96.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 600 mg (3.2 mmol) of 3-hydroxyimino-2-methoxyimino-N,N-dimethylbutyramide in 20 ml of acetone, 500 mg (3.5 mmol) of 4-methylbenzylchloride and 660 mg (4.8 mmol) of potassium carbonate were added and the mixture was heated under reflux for 16 hours. The reaction mixture was combined with 30 ml of water and extracted three times with 30 ml of diethylether. After washing with water and a saturated aqueous sodium chloride, the mixture was dried over with anhydrous magnesium sulfate and then the solvent was distilled off. The residue thus obtained was purified by a column chromatography on a silica gel (n-hexane/ethyl acetate) to obtain 900 mg (yield: 96%) of 3-(4-methylbenzyloxyimino)-2-methoxyimino-N,N-dimethylbutyramide as a colorless crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. extractionextracted three times with 30 ml of diethylether
  4. washAfter washing with water
  5. dry with materiala saturated aqueous sodium chloride, the mixture was dried over with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue thus obtained
  8. customwas purified by a column chromatography on a silica gel (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4439910297a7458ab185eeef33af6f63
Source dataset
uspto-grants-2001_06
Patent number
US06251949B1

Linked notes

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