Preparation of 5-amino 1,2,4-triazole-3-sulfonamides and...

Details Preparation of 5-amino 1,2,4-triazole-3-sulfonamides and... Preparation of 5-amino 1,2,4-triazole-3-sulfonamides and...

C - Chemistry, Metallurgy

07

D

260/313.3, 260/2

C07D 249/14 (2006.01) C07D 401/12 (2006.01)

Patent

CA 2005884

A process for preparing 5-amino-1,2,4-triazole-3- sulfonamides of formula I, which are intermediates for substituted 1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamide herbicides, in two steps from 5-amino-3-mercapto-1,2,4- triazole by chlorination in a medium containing an aqueous acid to obtain 5-amino-3-chlorosulfonyl-1,2,4-triazole and subsequent condensation of this intermediate with substituted anilines is disclosed. The condensation reaction takes place either in the presence or absence of an acid scavenging base. Novel intermediates are also provided. The process may be represented by the following reaction sequence: (see fig. I) + (see fig. II) (see fig. III) Image Image Image

Méthode de préparation de 5-amino-1,2,4-triazole-3-sulfonamides de formule I, intermédiaires pour herbicides à base de 1,2,4-triazolo¢1,5-a!pyrimidine-2-sulfonamide, en deux étapes à partir de 5-amino-3-mercapto-1,2,4- triazole par chloration dans un milieu renfermant un acide aqueux, afin d'obtenir le 5-amino-3-chlorosulfonyl-1,2,4-triazole, dont la condensation ultérieure avec des dérivés de substitution d'anilines est divulguée. La réaction de condensation a lieu en présence ou en l'absence d'une base neutralisant l'acide. De nouveaux intermédiaires sont également présentés. Le procédé peut être représenté par la séquence réactionnelle suivante : (voir fig. I) (voir fig. II) (voir fig. III) Image Image Image .

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