N-arylsulfilimine compounds and their use as catalysts in the preparation of N-arylarylsulfonamide compounds
AssigneeDow AgroSciences LLC
InventorsJames W. Ringer, Carmen A. Scott, Douglas L. Pearson, 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.
Claims20
A process for the preparation of an N-arylarylsulfonamide compound of the formula:
- Q-SO.sub.2 NH-AR
- wherein
- Q and AR each independently represents an aromatic hydrocarbyl or aromatic heterocyclyl moiety
- which comprises combining a sulfonyl chloride compound of the formula:
- Q-SO.sub.2 Cl
- wherein Q is defined as above
- with an amine compound of the formula:
- AR-NH.sub.2
- wherein AR is defined as above
- in the presence of an aromatic tertiary amine base and an added catalytic amount of an 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 an aromatic hydrocarbyl or aromatic heterocyclyl moiety.
The method of use of an N-arylsulfilimine compound of the formula:
- ##STR16## wherein R represents methyl, ethyl, or n-propyl;
- R' represents R, phenyl or benzyl or R and R' together represent tetramethylene;
- and
- AR' represents an aromatic hydrocarbyl or aromatic heterocyclyl moiety
- to catalyze the reaction between an aromatic sulfonyl chloride compound of the formula:
- Q-SO.sub.2 Cl
- wherein Q represents an aromatic hydrocarbyl or aromatic heterocyclyl moiety
- with an aromatic amine compound of the formula:
- AR-NH.sub.2
- wherein AR represents an aromatic hydrocarbyl or aromatic heterocyclyl moiety
- to obtain an N-arylarylsulfonamide compound of the formula:
- Q-SO.sub.2 NH-AR
- wherein Q and AR are as defined above.
Dependencies are inferred from the claim text.