Dimethyl Sulfate → 2-(Methoxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide

HRID 1078476Notes

Reaction equation

HRID 1078476 reaction equation
[CH3:1][NH:2][C:3](=[O:19])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.Cl.[NH2:21]O.[C:23](=[O:26])([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CO.CN(C)C=O.O>[CH3:1][NH:2][C:3](=[O:19])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:21][O:26][CH3:23]

Participants

8

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 11780091N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide

Product 1

HCID 864032-(Methoxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamideYield 47.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide (1.50 g) and hydroxylamine hydrochloride (0.69 g) in methanol (10 ml) was refluxed for 220 minutes while stirring, and water (75 ml) was added to the reaction mixture, followed by extraction with dichloromethane twice (150 ml and 100 ml). The organic layer was washed with water (75 ml) and dried over anhydrous sodium sulfate. Upon filtration, the filtrate was concentrated under reduced pressure to give a crystalline residue. The residue was combined with dimethylformamide (DMF) (7 ml), potassium carbonate (1.6 g) and dimethyl sulfate (0.58 ml) and stirred overnight. The reaction mixture was treated in the same manner as in Example 2 to give 0.80 g of the objective compound as an isomeric product.

Workup

  1. extractionfollowed by extraction with dichloromethane twice (150 ml and 100 ml)
  2. washThe organic layer was washed with water (75 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationUpon filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give a crystalline residue
  7. stirringstirred overnight
  8. additionThe reaction mixture was treated in the same manner as in Example 2

Sources & evidence

ORD record
ord-fb274fc0238d45ffb63d6916aaeeb6c3
Source dataset
uspto-grants-1996_08
Patent number
US05548078

Reaction notes

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