Phosphorus oxychloride → HCID 59580177, Verbindung

HRID 2189957Notizen

Reaktionsgleichung

[CH3:1][CH:2]([NH2:14])[CH2:3][O:4][C:5]1[C:10]([Br:11])=[CH:9][C:8]([Br:12])=[CH:7][C:6]=1[Br:13].[F:15][CH:16]([F:26])[C:17]1[C:21]([C:22](O)=[O:23])=[CH:20][N:19]([CH3:25])[N:18]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1.O>[CH3:1][CH:2]([NH:14][C:22]([C:21]1[C:17]([CH:16]([F:26])[F:15])=[N:18][N:19]([CH3:25])[CH:20]=1)=[O:23])[CH2:3][O:4][C:5]1[C:6]([Br:13])=[CH:7][C:8]([Br:12])=[CH:9][C:10]=1[Br:11]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A mixture of 0.3 g (0.8 mmol) 1-methyl-2-(2,4,6-tribromo-phenoxy)-ethylamine (compound Z1.193, prepared as described in example P7) and 0.15 g (0.9 mmol) 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid in 2 ml pyridine under a nitrogen atmosphere is cooled to 0° C. Phosphorus oxychloride (0.08 ml, 0.9 mmol) is added dropwise and the reaction mixture is stirred at 80° C. for 12 h. The reaction mixture is diluted with water and 3-times extracted with ethyl acetate. The combined ethyl acetate layers are washed with 1.5 N HCl, saturated NaHCO3, water and brine, dried over sodium sulphate and evaporated to dryness. The residue is purified by column chromatography (using 60-120 mesh-silica gel in hexane; eluent: ethyl acetate) to yield 0.12 g 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-methyl-2-(2,4,6-tribromo-phenoxy)-ethyl]-amide (27% of theory) as a yellow solid.

Aufarbeitung

extractionextracted with ethyl acetate
washThe combined ethyl acetate layers are washed with 1.5 N HCl, saturated NaHCO3, water and brine
dry with materialdried over sodium sulphate
customevaporated to dryness
customThe residue is purified by column chromatography (using 60-120 mesh-silica gel in hexane; eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-7bf893e4eeaa4b9487a7427c8353a197
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08324263B2

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