Base-Catalyzed Reaction of Cyanoalkylphosphonates with Methanol

The equilibrium conversion of nitriles in the reaction of cyanoalkylphosphonates with methanol in the presence of sodium methylate, as determined by potentiometric titration with perchloric acid in nitromethane, varies from 58 to 17.7%. The practical yields of imidates were evaluated by a preparative procedure of isolation of purified imidates from the reaction mixtures (56-14%). Because of the low conversions of nitriles, the reaction is expedient to use only for preparing alkyl (dialkoxyphosphoryl)acetimidates.