Hydrochloric Acid → HCID 76309304, compound

HRID 1779713Notes

Reaction equation

HRID 1779713 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[N:18][O:19][CH3:20])[C:15]([NH2:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[C:14](=[N:18]\[O:19][CH3:20])/[C:15]([NH2:17])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 539671372-(2-Phenoxyphenyl)-2-methoxyiminoacetamide

Product 1

HCID 76309304HCID 76309304, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(2-phenoxyphenyl)-2-methoxyiminoacetamide (E/Z=24/76) (5.05 g, 18.7 mmol) was dissolved in acetone (19 ml). Conc. hydrochloric acid (1.56 ml) was added, and the mixture was heated under reflux for 3 hours. After completion of the reaction, the reaction mixture was neutralized with a saturated aqueous solution of sodium bicarbonate and extracted with ether. The ether layer was washed with water and saturated brine, 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-phenoxyphenyl)-2-methoxyiminoacetamide (4.50 g, Yield: 89.1%, E/Z=96/4).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ether
  5. washThe ether layer was washed with water and saturated brine
  6. dry with materialdried 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-863a1caab5b64ab5b536b5e615ade5c5
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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