Hydrochloric Acid → Dimoxystrobin

HRID 1756738Notes

Reaction equation

HRID 1756738 reaction equation
[CH3:1][NH:2][C:3](=[O:24])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[CH3:23])=[N:5]\[O:6][CH3:7].Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][NH:2][C:3](=[O:24])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[CH3:23])=[N:5]/[O:6][CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 9797414(E)-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyimino-N-methylacetamide

Product 1

HCID 10936292DimoxystrobinYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Z)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (650 mg, 2 mmol) was dissolved in methylene chloride (4 ml). Conc. hydrochloric acid (0.16 ml) was added, and the mixture was stirred at room temperature for 120 hours. After completion of the reaction, a saturted aqueous solution of sodium bicarbonate (50 ml) was added for neutralization. The resulting mixture was extracted with methylene chloride (100 ml), washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (650 mg, Yield: 100%, E/Z=97/3) as colorless crystals.

Workup

  1. customAfter completion of the reaction
  2. extractionThe resulting mixture was extracted with methylene chloride (100 ml)
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc0f1a82486d4f18a93c154ea66b23ac
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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