Hydrochloric Acid → Desmethylamino Methoxy (E)-Metominostrobin

HRID 266414Notes

Reaction equation

HRID 266414 reaction equation
[OH:1]/[N:2]=[C:3](\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)/[C:4](O)=[O:5].[CH3:20][O-:21].[Na+].[CH3:23]OS(OC)(=O)=O.Cl>CS(C)=O.C1(C)C=CC=CC=1.O>[CH3:20][O:21][C:4](=[O:5])/[C:3](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:2]/[O:1][CH3:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 10942334Sodium MethoxideHCID 88386642(2E)-2-hydroxyimino-2-(2-phenoxyphenyl)acetic acid

Product 1

HCID 10803045Desmethylamino Methoxy (E)-MetominostrobinYield 73.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of E-α-hydroxyimino-2-phenoxyphenylacetic acid (10.00 g, 0.0389 mole) in dimethyl sulfoxide (50 ml) and toluene (50 ml) was added sodium methoxide (4.83 g, 0.0894 mole) with stirring under ice cooling, and the mixture was stirred at room temperature for 20 minutes and then cooled. Dimethylsulfate (11.28 g, 0.0894 mole) was added at 6°-18° C. over 6 minutes, followed by stirring at room temperature for 4.5 hours. After completion of the reaction, conc. hydrochloric acid (1.2 ml) and water (100 ml) were added to the reaction mixture with stirring under ice cooling, followed by extraction with toluene. The extract was washed with water and concentrated under reduced pressure, and then the resulting residue was recrystallized (methanol) to obtain E-α-methoxyimino-2-phenoxyphenylacetic acid methyl ester (8.11 g, yield: 73.1%) as colorless crystals (melting point: 107°-109° C.).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. temperaturecooled
  3. stirringby stirring at room temperature for 4.5 hours
  4. additionwere added to the reaction mixture
  5. stirringwith stirring under ice cooling
  6. extractionfollowed by extraction with toluene
  7. washThe extract was washed with water
  8. concentrationconcentrated under reduced pressure
  9. customthe resulting residue was recrystallized (methanol)

Sources & evidence

ORD record
ord-a4a3671a17294b89ab6812f2ac740e2e
Source dataset
uspto-grants-1997_07
Patent number
US05650539

Reaction notes

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