Process for the preparation of alkoxytriazolinones

US5599945A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Heinz-Jurgen Wroblowsky · Langenfeld, DE
• Klaus K onig · Odenthal, DE

Key dates

• Filing date: Sep 15, 1995
• Grant date: Feb 4, 1997
• Expiry date: Sep 15, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C281/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Alkoxytriazolinones of the formula (I), ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, PA1 (which can be used as intermediates for the preparation of herbicidal active compounds) are obtained in good yields and in high purity by reacting iminocarbonic diesters (II) with carbazinic esters (III) ##STR2## in which R.sup.2 and R.sup.3 in each case represent, for example, alkyl or aryl, at -20.degree. C. to +120.degree. C. (1st step) and subjecting the semicarbazide derivatives (IV) formed in this process with elimination of R.sup.2 --OH ##STR3## to a cyclizing condensation reaction in the presence of a base at 20.degree. C. to 150.degree. C. with elimination of R.sup.3 --OH, if appropriate (2nd step) and, finally, by reacting the resulting 5-alkoxytriazolinones of the formula (V) with an alkylating agent of the formula R.sup.1 --X (VI) at 0.degree. C. to 150.degree. C., if appropriate in the presence of a base (3rd step: highly selective 4-alkylation).