Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methoxy-N-methyl-5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide

HRID 1296351

Reaktionsgleichung

C([Mg]Cl)(C)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:16]=[C:15]([C:25](OCC)=[O:26])[C:14]=2[CH3:30])=[CH:9][CH:8]=1.Cl.[CH3:32][NH:33][O:34][CH3:35]>C1COCC1>[CH3:35][O:34][N:33]([CH3:32])[C:25]([C:15]1[C:14]([CH3:30])=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=2)[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[N:16]=1)=[O:26]

Komponenten

Reaktionsbedingungen

Temperatur: -25 °C

Versuchsvorschrift

Isopropylmagnesium chloride (15 ml, 30 mmol) was added dropwise over a 10 to 15 minute period to a stirred solution of ethyl 5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate (8.15 g, 21.7 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.51 g, 15.5 mmol) in THF at −25° C. After stirring for an additional 15 minutes at −25° C., the reaction mixture was quenched with saturated aqueous NH4Cl and then extracted with methyl-tert-butyl ether. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the title compound I-1a as a golden oil (8.76 g).

Aufarbeitung

customthe reaction mixture was quenched with saturated aqueous NH4Cl
extractionextracted with methyl-tert-butyl ether
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-d5e959fcaacf46199ae8e563b0a306ab
Quelldatensatz: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07247628B2

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