Hydrochloric Acid → (2E)-2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxyiminoacetamide

HRID 1756733Notes

Reaction equation

HRID 1756733 reaction equation
C(Cl)Cl.Cl.[CH3:5][C:6]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[N:20][O:21][CH3:22])[C:17]([NH2:19])=[O:18]>O>[CH3:5][C:6]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[C:16](=[N:20]\[O:21][CH3:22])/[C:17]([NH2:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 542571262-[2-(2,5-Dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide

Product 1

HCID 15790186(2E)-2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxyiminoacetamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methylene chloride (60 ml) and conc. hydrochloric acid (20 ml) were added to 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (Z=at least 98%) (6.25 g, 0.02 mol), and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, water (150 ml) was added. The mixture was extracted with methylene chloride (100 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crystals. The crystals were recrystallized from n-hexane/ethyl acetate to give (E)-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (5.41 g, Yield: 86.7%) as colorless crystals.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with methylene chloride (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give crystals
  6. customThe crystals were recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-13267f423d7345c4b0412014e5750432
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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