1,2-Dichloroethane → HCID 22419013, compound

HRID 1720568Notes

Reaction equation

HRID 1720568 reaction equation
ClCCCl.S(Cl)(Cl)=O.[Cl:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2/[C:24](=[N:28]\[O:29][CH3:30])/[C:25]([OH:27])=O)=[CH:14][CH:13]=[CH:12][N:11]=1.[CH3:31][NH2:32].CO>O.CN(C)C=O>[Cl:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2/[C:24](=[N:28]\[O:29][CH3:30])/[C:25]([NH:32][CH3:31])=[O:27])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 24386Thionyl ChlorideHCID 57454252Monomethylamine methanolHCID 88287593HCID 88287593, compound

Product 1

HCID 22419013HCID 22419013, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,2-Dichloroethane (1 ml), thionyl chloride (0.03 g, 0.28 mmol) and dimethylformamide (DMF)(0.01 ml) were added to (E)-2-(2-chloro-3-pyridyloxymethyl)-α-methoxyiminophenylacetic acid (0.05 g, 0.14 mmol). The mixture was stirred under reflux for 1 hour. To the reaction mixture was added 40% methylamine/methanol solution (1 ml) under ice-cooling. The mixture was stirred at 0° C. for 1 hour. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with methylene chloride (50 ml) twice. The methylene chloride layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give (E)-2-[2-(2-chloro-3-pyridyloxymethyl)phenyl]-2-methoxyimino-N-methylacetamide (0.02 g, 42.8 %) as colorless crystals.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooling
  3. stirringThe mixture was stirred at 0° C. for 1 hour
  4. additionwas added
  5. extractionthe mixture was extracted with methylene chloride (50 ml) twice
  6. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-a8293d092e944438b7aaff5e6cd7eb91
Source dataset
uspto-grants-1996_04
Patent number
US05506358

Reaction notes

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