Ethyl 2-(methoxyimino)-4-oxopentanoate → Ethyl 3-methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxylate

HRID 598193

Reaktionsgleichung

Reaktionsgleichung von HRID 598193
CON=[C:4]([CH2:10][C:11](=O)[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=1[NH:24][NH2:25]>C(O)(=O)C.C(OCC)(=O)C>[CH3:12][C:11]1[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:24]([C:17]2[C:16]([Cl:15])=[CH:21][C:20]([Cl:22])=[CH:19][C:18]=2[Cl:23])[N:25]=1

Komponenten

5

Edukt 2

HCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoateHCID 3014122(2,4,6-Trichlorophenyl)hydrazine monohydrochloride

Produkt 1

HCID 67267631Ethyl 3-methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxylateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of ethyl 2-(methoxyimino)-4-oxopentanoate (2.00 g, 10.7 mmol) and 2,4,6-trichlorophenylhydrazine hydrochloride (3.39 g, 16.0 mmol) in acetic acid (40 ml) and 2-methoxuethanol (20 ml) was stirred for 20 h at 105° C. The solvent was under vacuum and the residue was dissolved in ethyl acetate. The organic solution was washed with 0.2N HCl and water, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with 10% ethyl acetate/n-hexane to give the title compound (1.50 g, 42%).

Aufarbeitung

  1. washThe organic solution was washed with 0.2N HCl and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 10% ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d7df74e885d3482785c853c60c336a87
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897607B2

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