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Hydrochloric Acid → Desmethylamino Methoxy (E)-Metominostrobin

HRID 266414
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 266414
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

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

Produkt 1

HCID 10803045Desmethylamino Methoxy (E)-MetominostrobinAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a4a3671a17294b89ab6812f2ac740e2e
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05650539

Notizen zur Reaktion

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