Synthesis Research Of 6-Methanesulfonylaminomethyl Benzo[d]isothiazol-3(2H)-one 1,1-dioxide

6-(aminomethyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide(5-methanesulfonamidomethyl saccharin)is one of saccharin derivatives,and also an important organic chemical intermediates,which is widely used in pesticide,medicine,and synthetic materials industry,especially in the synthesis of pesticides.It is a key intermediate in the synthesis of selective herbicides of Mesosulfuron-methyl.Sulfonylurea herbicides are considered as the most efficient and biodegradable representatives of pesticide.This kind of pesticide overcomes the disadvantage of traditional ones,such as large working dosage,difficult degradation and long residue period.Therefore,the development of novel sulfonylurea herbicides have been attractting more and more attention.As the key intermediate of sulfonylurea herbicides,saccharin and its derivatives have been widely researched.In this paper,we designed two routes for synthesis of 5-methanesulfonamidomethylsaccharin,which is an important intermediates for the synthesis of novel sulfonylurea herbicide Mesosulfturon-methyl.The first route started from 4-methybenzoic acid.After sulfonation,ammoniation,esterification,ammoniation,oxidation,dehydration,catalytic hydrogenation,we got the desired compound in totally yield of X.Through the experimental investigation,it was found that the steps of this route were easy to operate.Although the intermediate of each step did not need purification,the reaction conditions were relatively harsh,and ultimately lead to the increaseof industrial production costs.The second one obtained the compound from 4-methybenzonitrile as the starting material in seven steps(nitrification,oxidation,esterification,catalytic hydrogenation,methanesulfonylation,diazotization-chlorosulfonation,ammoniation)with totally yield of X.It was found that the reaction conditions were relatively mild in every step,and the purity and yield of the desired productwere relatively higher.In this paper,all intermediates and targeted compounds were characterized by liquid chromatograph,LC-Mass and NMR.We aim at choosing a suitable process for industrial production by optimizing and comparing these two methods and provide a reference for industrial production...