Preparation of novel 5-acyloxy-4-(5H)-oxazolonium salts suited for use as intermediates for triazinone herbicides

US4594427A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Gerhard Bonse · Neunburg vorm Wald, DE
• Gerhard Marzolph · Cologne, DE
• Heinz U. Blank · Odenthal, DE

Key dates

• Filing date: Mar 22, 1982
• Grant date: Jun 10, 1986
• Expiry date: Mar 22, 2002

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D263/44
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Novel 5-acyloxy-4(5H)-oxazolonium salts of the formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic group with up to 12 carbon atoms, an optionally substituted cycloalkyl group with 3 to 10 carbon atoms, an optionally substituted phenyl or naphthyl group or an optionally substituted heterocyclic group and PA0 R.sup.2 and R.sup.3 are identical or different and represent a hydrogen atom or an optionally substituted aliphatic group with up to 8 carbon atoms or an optionally substituted phenyl group and PA0 X.sup..crclbar. represents the anion of an inorganic or organic acid having a pK.sub.a value of less than 2, are obtained in solution when an acyl cyanide of the general formula EQU R.sup.1 --CO--CN (II) is reacted with a carboxylic acid anhydride of the general formula EQU R.sup.2 --CO--O--CO--R.sup.3 (III) wherein PA0 R.sup.1, R.sup.2 and R.sup.3 each have the abovementioned meaning, in the presence of one or more inorganic or organic acids having a pK.sub.a value of less than 2, and if appropriate in the presence of a solvent, and if appropriate at a temperature between 0.degree. and 120.degree. C. The novel oxazolonium salts (I) can be used as interme…