This invention relates to novel N-(N'-methylenepyrrolidonyl)-2-substituted anilines which are useful intermediates in the synthesis of herbicides. The intermediate compounds of the invention have the formula: ##STR1## Where R is alkyl, C.sub.1 -C.sub.6, alkenyl, C.sub.3 -C.sub.5, alkyleneoxyalkyl, --(CH.sub.2).sub.n OR", where n=1-3, and R" is alkyl, C.sub.1 -C.sub.3, and cycloalkyl, ##STR2## where n'=0-3, R' is hydrogen or alkyl, C.sub.1 -C.sub.3, and, Y is oxygen or sulfur.
Process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines
申请人:GAF Corporation
公开号:US04203901A1
公开(公告)日:1980-05-20
This invention relates to a process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines in high yield. The products are useful intermediates in the synthesis of herbicides. The process comprises reacting substantially equivalent molar concentrations of a 2-substituted aniline, as defined herein, with N-methylolpyrrolidone in an aromatic hydrocarbon solvent in the absence of an acid or base catalyst at a reflux temperature of 80.degree.-140.degree. C. while simultaneously and continuously distilling out from the reaction mixture an azeotrope consisting essentially of water and solvent until substantially all the water produced during the reaction has been removed thereby, and, thereafter, crystallizing the product from the remaining solution.