Toluene → Dimoxystrobin

HRID 1779726Notes

Reaction equation

HRID 1779726 reaction equation
CCl.[OH-].[K+].[C:5]1(C)C=CC=CC=1.[CH3:12][C:13]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1/[C:23](=[N:27]\[O:28][CH3:29])/[C:24]([NH2:26])=[O:25]>O>[CH3:12][C:13]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1/[C:23](=[N:27]\[O:28][CH3:29])/[C:24]([NH:26][CH3:5])=[O:25]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6327Methyl ChlorideHCID 14797Potassium HydroxideHCID 15790186(2E)-2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxyiminoacetamide

Product 1

HCID 10936292DimoxystrobinYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Methyl chloride (0.45 g, 9.0 mmol), 85% potassium hydroxide (0.30 g, 4.5 mmol) and toluene (9 ml) were added to (E)-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (0.94 g, 3.0 mmol). The mixture was stirred at 100° C. for 1 hour. After completion of the reaction, water (100 ml) was added. The mixture was extracted with ether (100 ml), 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-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyimino-N-methylacetamide (0.88 g, Yield: 90.2%) as colorless crystals. mp 136°-137° C.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ether (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-20b62961df7a47b6afdb1b999f487c16
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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