Process for the preparation of alkoxytriazolinones

Details Process for the preparation of alkoxytriazolinones Process for the preparation of alkoxytriazolinones

C - Chemistry, Metallurgy

07

D

C07D 249/12 (2006.01) C07C 281/04 (2006.01)

Patent

CA 2158712

Alkoxytriazolinones of the formula (I), Image in which R1 and R2 independently of one another represent in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, (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) Image in which R2 and R3 in each case represent, for example, alkyl or aryl, at -20°C to + 120°C (1st step) and subjecting the semicarbazide derivatives (IV) formed in this process with elimination of R2-OH Image to a cyclizing condensation reaction in the presence of a base at 20°C to 150°C with elimination of R3-OH, if appropriate (2nd step) and, finally, by reacting the resulting 5-alkoxytriazolinones of the formula (V)[=formula (I) where R1 = H] with an alkylating agent of the formula R1-X(VI)[X, for example, = halogen or -OSO2OR1] at 0°C to 150°C, if appropriate in the presence of a base (3rd step: highly selective 4-alkylation).

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