N-arylsulfilimine compounds and their use as catalysts in the preparation of N-arylarylsulfonamide compounds
AssigneeDow AgroSciences LLC
InventorsJames W. Ringer, Douglas L. Pearson, Carmen A. Scott, Anne P. Wallin
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Abstract
N-arylsulfilimine compounds, such as S,S-dimethyl-N-(2,6-dichlorophenyl)sulfilimine, were prepared and found to catalyze the reaction of aromatic sulfonyl chloride compounds, such as 2-chlorosulfonyl-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine, with aromatic amine compounds, such as 2,6-dichloroaniline, to form N-arylarylsulfonamide compounds, such as N-(2,6-dichlorophenyl)-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine-2 -sulfonamide. The aryl moiety of the N-arylsulfilimine catalyst and the aryl moiety of the aromatic amine compound were generally chosen to be identical.
Claims7
A substituted N-arylsulfilimine compound of the formula:
- ##STR13## wherein R represents methyl, ethyl, or n-propyl;
- R' represents R, benzyl, or phenyl;
- or R and R' together represent tetramethylene;
- and
- AR' represents a phenyl moiety of the formula:
- ##STR14## wherein A represents F, Cl, Br, NO.sub.2, CN, C.sub.1 -C.sub.4 fluoroalkyl, CO.sub.2 (C.sub.1 -C.sub.4 alkyl), CONH(C.sub.1 -C.sub.4 alkyl), CON(C.sub.1 -C.sub.4 alkyl).sub.2, SO.sub.2 (C.sub.1 -C.sub.4 alkyl), or SO.sub.2 (C.sub.1 -C.sub.4 fluoroalkyl);
- B represents C.sub.1 -C.sub.4 alkyl, F, Cl, Br, O(C.sub.1 -C.sub.4 alkyl), O(C.sub.1 -C.sub.4 fluoroalkyl), S(C.sub.1 -C.sub.4 alkyl), S(C.sub.1 -C.sub.4 fluoroalkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2 ;
- or phenyl, phenoxy, or phenylthio each optionally possessing 1 to 3 substituents selected from the group consisting of F, Cl, Br, CN, CF.sub.3, NO.sub.2, and CH.sub.3 ;
- and
- D and J each independently represents H or CH.sub.3 with the proviso that at least one of D and J represents H.
Dependencies are inferred from the claim text.