摘要:
3-(2,4-Dichlorophenyl)-5-t-butyl-1,3,4-oxadiazol-2-ones of the formula: IN WHICH R represents a hydrogen atom or an alkoxy group containing one to four carbon atoms, which possess herbicidal properties, are prepared by a new process involving reaction of a halogenonitrobenzene of the formula: IN WHICH Y represents a halogen atom and R is as defined, with an alkali metal salt of 5-t-butyl-1,3,4-oxadiazol-2-one, reduction of the nitro group in the resulting 3-(2-chloro-4nitrophenyl)-5-t-butyl-1,3,4-oxadiazol-2-one, which may carry an alkoxy substituent R in the 5-position of the benzene ring, to a primary amino group, and replacement of the amino group in the resulting 3-(2-chloro-4-aminophenyl)-5-t-butyl-1,3,4-oxadiazol-2one by a chlorine atom by reaction of cuprous chloride with a diazonium salt derived from the amino compound. The process avoids the use of phosgene - an awkward reagent hitherto employed in the production of the 3-(2,4-dichlorophenyl)-5-t-butyl-1,3,4oxadiazol-2-ones.