Process for the preparation of the herbicide ethyl...

C - Chemistry – Metallurgy – 07 – D

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C07D 249/12 (2006.01)

Patent

CA 2229563

A process is disclosed for the preparation of the herbicide ethyle a-2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2, 4-triazol-1-yl]-4-fluorobenzenepropionate by the simultaneous diazotization of 4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chloro- phenyl) -1H-1,2,4-triazole (the Amine) and arylation of ethyl acrylate with the diazotized Amine. In the process the following reagents are added in sequence and, under specified conditions, to a cooled, stirred solution of the Amine in acetone: cuprous chloride, hydrochloric acid, ethyl acrylate, and sodium nitrite.

L'invention concerne un procédé de préparation de l'herbicide éthyle alpha -2-dichloro-5-[4-difluorométhyl)-4,5-dihydro-3-méthyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorobenzenepropionate par diazotation simultanée de 4-difluorométhyl-4,5-dihydro-3-méthyl-5-oxo-1-(5-amino-2-fluoro-4-chloro-phényl)-1H-1,2,4-triazole (qui est l'amine) et arylation de l'acrylate d'éthyle avec l'amine diazotée. Dans le cadre de ce procédé, les réactifs ci-après sont ajoutés successivement et dans des conditions spécifiques à une solution refroidie et agitée de l'amine dans l'acétone: chlorure cuivreux, acide chlohydrique, acrylate d'éthyle et nitrite de sodium.

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