51291-82-8

Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXY-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE is used as an intermediate in the synthesis of 4-Desmethyl Flucarbazone Sodium Salt (D343230), which is an impurity of Flucarbazone (F148340) and Flucarbazone-sodium (F421125). These compounds have potential applications in the development of new pharmaceuticals, contributing to the advancement of drug discovery and therapeutic treatments.
Used in Agricultural Industry:
5-METHOXY-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE is used as a key component in the synthesis of Flucarbazone, which is a herbicide used for agricultural purposes. Flucarbazone helps in controlling and managing unwanted plant growth, ensuring better crop yield and quality. Its use in agriculture contributes to more efficient and sustainable farming practices.
Additionally, Flucarbazone is also recognized as an antiparasitic agent, which means that 5-METHOXY-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE, through its role in the synthesis of Flucarbazone, indirectly contributes to the development of antiparasitic treatments. This highlights the compound's potential in addressing various health and environmental concerns through its applications in different industries.

InChI:InChI=1/C3H5N3O2/c1-8-3-4-2(7)5-6-3/h1H3,(H2,4,5,6,7)

Upstream product

• 67-56-1 methanol 
• 177030-58-9 ethyl N'-(α-amino-α-methoxy-methylene)-hydrazine-N-carboxylate 
• 39142-28-4 (Methoxythiocarbonyl)carbamidsaeure-methylester 
• 4114-31-2 ethylhydrazine carboxylate 

Downstream Products

• 258885-98-2 4-(3-bromobenzyl)-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 258886-07-6 4-(5-bromo-2-fluorobenzyl)-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 258885-99-3 5-methoxy-4-(3-phenoxybenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 258885-96-0 5-methoxy-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 258886-06-5 4-(5-bromo-2-chlorobenzyl)-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 258886-14-5 5-methoxy-4-{1-(2-methyl-5-phenyl)phenylethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 258886-02-1 4-(3-formylbenzyl)-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 135302-13-5 5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one 

Relevant academic research and scientific papers

Chlorination and subsequent cyclization to 1,3,4-oxadiazoles of N1-acyl-N3-cyanoguanidines and rerated compounds

N1-Acyl-, N1-alkoxycarbonyl-, and N1-(N,N-dialkylcarbamoyl)guanidines bearing electron-withdrawing cyano or sulfonyl group at the N3-position were found to provide corresponding rearranged products, 1,3,4-oxadiazoles, when these guanidines were chlorinated by sodium hypochlorite followed by treating with base. Assignments of obtained compounds were accomplished by means of some reactions such as acid hydrolysis, alkoholysis, and catalytic hydrogenations, and of MS spectra.

Process for the manufacture of substituted triazolinones

The present invention relates to a process for manufacturing substituted triazolinones, which are intermediates in the preparation of herbicidally active compounds. In particular, this invention relates to the alkylation of a non-alkylated triazolinone intermediate product, wherein the improvement comprises conducting the alkylation reaction under pH controlled conditions. In a preferred embodiment, the invention relates to the preparation of a 5-alkoxy(or aryloxy)-2,4-dihydro-3H-1,2,4-triazol-3-one, and the alkylation of this non-alkylated triazolinone intermediate product, to produce a 5-alkoxy(or aryloxy)-4-alkyl-2,4-dihydro-3H-1,2,4-triazol-3-one.

Process for preparing alkoxytriazolinones

Alkoxytriazolinones of the formula (I) ?known for example as intermediates for preparing agrochemically active compounds! STR1 wherein R represents an alkyl group, an alkenyl group, an alkinyl group, a cycloalkyl group, a cycloalkylalkyl group, an aryl group or an arylalkyl group, any of which may be substituted, are prepared by reacting a) thioimidodicarboxylic diesters of the general formula (II) STR2 wherein R is as defined above and R1 represents an alkyl group, an arylalkyl group or an aryl group, any of which may be substituted, with b) hydrazine, hydrazine hydrate or an acid adduct of hydrazine. The reaction is conducted i) in the presence of a diluent and, optionally, in the presence of a basic reaction auxiliary, and ii) at temperatures between -10° C. and +100° C.

Process for the preparation of alkoxytriazolinones

Alkoxytriazolinones of the formula (I), STR1 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) STR2 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 STR3 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) with an alkylating agent of the formula R1 --X (VI) at 0° C. to 150° C., if appropriate in the presence of a base (3rd step: highly selective 4-alkylation).