Potassium Carbonate → 2-[2-[[(E)-benzylideneamino]oxymethyl]phenyl]-2-methoxy-N-methylacetamide

HRID 617392Notes

Reaction equation

HRID 617392 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([O:14][CH3:15])[C:10]([NH:12][CH3:13])=[O:11].S(Cl)(Cl)=O.[CH:20](=[N:27]O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O.O>[CH:20](=[N:27]/[O:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([O:14][CH3:15])[C:10]([NH:12][CH3:13])=[O:11])\[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 12143(Z)-Benzaldehyde oximeHCID 24386Thionyl ChlorideHCID 702393162-hydroxymethyl-alpha-methoxy-N-methyl-phenylacetamide

Product 1

HCID 763342412-[2-[[(E)-benzylideneamino]oxymethyl]phenyl]-2-methoxy-N-methylacetamideYield 51.2%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-hydroxymethyl-α-methoxy-N-methyl-phenylacetamide (0.42 g, 2.0 mmol) in tetrahydrofuran (4 ml) was stirred at 0° C., and thionyl chloride (0.17 ml, 2.4 mmol) and one drop of N,N-dimethylformamide were added. The mixture was stirred at room temperature for 2 hours, and water was added. The resulting mixture was extracted with ether, washed with saturated brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude product (0.38 g) as an oil. Benzaldehyde oxime (0.37 g, 3.1 mmol) and potassium carbonate (0.55 g, 4.0 mmol) were added to a solution of the crude product in N,N-dimethylformamide (6 ml), and the mixture was stirred at room temperature for 3 days. Water was added, and the mixture was extracted with ether and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=13/7) to give the desired compound (E)-2-benzylideneaminooxymethyl-α-methoxy-N-methylphenylacetamide (0.32 g, 51%) as white crystals.

Workup

  1. extractionThe resulting mixture was extracted with ether
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave a crude product (0.38 g) as an oil
  6. stirringthe mixture was stirred at room temperature for 3 days
  7. extractionthe mixture was extracted with ether
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=13/7)

Sources & evidence

ORD record
ord-0d04b4f7c7cc4ee9878b3d0245a44f62
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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