Water → HCID 53739379, compound

HRID 1654448Notes

Reaction equation

HRID 1654448 reaction equation
[CH3:1][NH:2][C:3](=[O:17])[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[N:15][OH:16])=[N:5][O:6][CH3:7].C(=O)([O-])[O-].[K+].[K+].[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Cl.O>CN(C=O)C>[CH3:1][NH:2][C:3](=[O:17])[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[N:15][O:16][CH2:28][C:27]1[CH:30]=[CH:31][CH:32]=[C:25]([Cl:24])[CH:26]=1)=[N:5][O:6][CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12103m,alpha-DichlorotolueneHCID 136401234HCID 136401234, compound

Product 1

HCID 53739379HCID 53739379, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1 g (4.26 mmol) of N-methyl-2-{2-(hydroxyiminomethyl)phenyl}-2-methoxyiminoacetamide and 0.62 g (4.5 mmol) of potassium carbonate in 10 ml of DMF, was added 0.69 g (4.29 mmol) of 3-chlorobenzyl chloride and the mixture was stirred under heating at 110° C. for 3 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, successively washed with water and a saturated sodium chloride solution and dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was chromatographed over SiO2 to give 0.9 g of the title compound (yield: 58.8%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washsuccessively washed with water
  4. dry with materiala saturated sodium chloride solution and dried over anhydrous sodium sulfate
  5. concentrationAfter concentration in vacuo
  6. customthe residue was chromatographed over SiO2

Sources & evidence

ORD record
ord-da780ee4d8dc46d4b6ee26c6edb63141
Source dataset
uspto-grants-1995_04
Patent number
US05407902

Reaction notes

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