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Abstract

This provides the processes for the manufacture of thioethers and sulfoxides used as pesticides. Claim 5: A process comprising: (a) the halogenation and reduction of 4-nitropyrazole of formula (2) with concentrated hydrochloric acid at a temperature between about 10 ° C and about 20 ° C, with about 1 and 4 equivalents of triethylsilane and about 1 to 10 percent of the weight of palladium in alumina to produce 3-chloro-1H-pyrazol-4-amine hydrochloride of formula (1a); (b) the reaction of the compound of formula (1a) with activated carbonyl thioether X¹C (= O) C₁₋₄-alkyl-S-R¹ wherein X¹ is selected from Cl, OC (= O) C₁₋₄ alkyl, or a group forming an activated carboxylic acid and R¹ is selected from the group consisting of C halo haloalkyl and C₁₋₄ alkyl, C₃₋₆ halocycloalkyl to produce thioether of formula (3a); (c) heteroarylation of the compound of formula (3a) with a halopyridine in the presence of a copper salt, an amine and a base to produce thioether of formula (3b); (d) the alkylation of a thioether of formula (3b) with R²-X² in the presence of a base, wherein R² is selected from the group consisting of C₁₋₄ alkyl and C₂₋₄ alkynyl, and where X² is a group of output, to produce thioether of formula (3c).

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First Claim

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