(2,6-Dichlorophenyl)hydrazine monohydrochloride → 2-(2,6-Dichloro-phenyl)-4-isobutyl-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

HRID 2261737

Reaktionsgleichung

Reaktionsgleichung von HRID 2261737
[CH2:1]([O:3][C:4](=[O:17])[C:5](=NOC)[CH:6]([C:11](=O)[CH3:12])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2].Cl.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[NH:27][NH2:28]>C(O)(=O)C.COCCO>[CH2:1]([O:3][C:4]([C:5]1[N:27]([C:21]2[C:20]([Cl:19])=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:26])[N:28]=[C:11]([CH3:12])[C:6]=1[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:17])[CH3:2]

Komponenten

5

Edukt 2

HCID 2723909(2,6-Dichlorophenyl)hydrazine monohydrochlorideHCID 765400763-Acetyl-2-methoxyimino-5-methyl-hexanoic acid ethyl ester

Produkt 1

HCID 574432512-(2,6-Dichloro-phenyl)-4-isobutyl-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 3-acetyl-2-methoxyimino-5-methyl-hexanoic acid ethyl ester (1 g, 4.1 mmol), 2,6-dichlorophenylhydrazine hydrochloride (1.76 g, 8.2 mmol) in glacial acetic acid (10 mL) and 2-methoxy-ethanol (5 mL) is stirred at 105° C. for 3 hours. The reaction is concentrated and the residue is partitioned between EtOAc and 1N HCl. The organic layer is concentrated and purified by column chromatography (0-20% EtOAc in hexanes) to give the title product as an oil, 1.1 g (76%).

Aufarbeitung

  1. concentrationThe reaction is concentrated
  2. customthe residue is partitioned between EtOAc and 1N HCl
  3. concentrationThe organic layer is concentrated
  4. custompurified by column chromatography (0-20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e9867d0e83554934863d2c2d7f3150e3
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846960B2

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