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US 9,102,655 B2Granted
Processes for the preparation of pesticidal compounds
AssigneeDow AgroSciences LLC
InventorsQiang Yang, Beth Lorsbach, Gregory T. Whiteker, Gary Roth, Carl DeAmicis, Thomas P. Clark, Kaitlyn Gray, Belgin Canturk, Elisabeth J. Kane, Yu Zhang, Joseck M. Muhuhi
Life of this patent
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Abstract
The present application provides processes for making pesticidal compounds and compounds useful both as pesticides and in the making of pesticidal compounds.
Claims6
A process comprising:
- (a) halogenating and reducing 4-nitropyrazole to produce
- 3-chloro-1H-pyrazol-4-amine hydrochloride (1a)
- with concentrated hydrochloric acid at a temperature between about 10° C. and about 20° C. with between about 1 and about 4 equivalents of triethylsilane and about 1 to 10 weight percent palladium on alumina;
- (b) mono-acylating 3-chloro-1H-pyrazol-4-amine hydrochloride (1a) with acetic anhydride in the presence of a base to yield
- (c) reacting 1(b) with a suitable halopyridine in the presence of a copper salt, an amine, and a base, to yield N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide (1c)
- (d) reacting 1(c) with a suitable reducing agent in the presence of an acid to yield 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-amine (1d)
- (e) reacting 1(d) with a suitable activated carboxylic acid, carboxylic acid anhydride, or acid chloride of a carboxylic acid to yield thioether (1e)
- wherein, R1 is selected form the group consisting of C1-C4 haloalkyl and C1-C4 alkyl-C3-C6 halocycloalkyl.
5 more elements
Dependencies are inferred from the claim text.