PROCESS FOR HALOMETHYL ETHERS OF HYDROXYIMINOMETHYL QUATERNARY PYRIDINIUM SALTS

摘要

A halide salt of a 1-(hydroxyiminomethyl-1-pyridino)-3-(halomethyl)-2- oxapropane is prepared by adding a pyridinealdoxime to a bis-halomethylether in such a manner that the bis-halomethylether is maintained in excess throughout the addition. This procedure produces the halide salt of a 1-(hydroxyiminomethyl-1-pyridino)-3- (halomethyl)- 2-oxapropane in high yield and purity, which facilitates its use as an intermediate in the manufacture of an asymmetrically substituted 1,3-di(1-pyridino)-2-oxapropane , a class of compounds that are generally useful antidotes to various toxic agents. A prominent member of the class is the dimethylsulfonate salt of 1-(2-hydroxyiminomethyl-1- pyridino)-3-(4- carbamoyl-1-pyridino)-2-oxapropane. The use of mercaptoalkyl-functionalized polymers is disclosed as a preferred metal ion scavenger for a final purification step i n the manufacture of these compounds.