PRODUCTION OF 3-SUBSTITUTED PHENYL-5-ALKYLIDENE-1,3-OXAZOLIDINE-2,4-DIONE DERIVATIVE

摘要

PROBLEM TO BE SOLVED: To industrially advantageously obtain a compound capable of exhibiting strong herbicidal activity by only heating a metal compound as a catalyst by using a raw material capable of readily producing. ;SOLUTION: An N-substituted phenylcarbamic acid ester of formula I (Ar is asubstituted phenyl; R¹ is a 1-6C alkyl or benzyl) is reacted with a 3-alkoxy-2- hydroxyalkanoic acid ester of formula II (R² and R³ are H, a 1-12C alkyl; R⁴ and R⁵ are each a 1-6C alkyl) in the presence of a metal compound catalyst by heating to provide the objective compound of formula III. A fluoride, chloride, bromide, etc., of iron or tin is preferably used as the metal compound. The reaction is preferably further carried out in the presence of a tertiary amide. The compound of formula II is obtained by reacting a glycidic ester of a compound of formula IV with an alcohol of the formula, R⁵OH (R⁵ is an alkyl) in the presence of an acid catalyst. The compound of formula I is readily obtained by reacting the corresponding aniline derivative with chloroformic acid ester in the presence of a base.;COPYRIGHT: (C)1997,JPO