Preparation method of triazinone ring

Abstract

A preparation method of a triazinone ring relates to the technical field of veterinary drugs, and comprises the following steps: carrying out a diazo condensation reaction on a condensation compound aniline and potassium ethyl malonate, carrying out an amidation reaction with sodium cyanate under an acidic condition, adding acetic acid and sodium acetate, heating, heating, and carrying out a cyclization reaction to obtain a triazinone compound. According to the method, operations such as filtration and separation are not needed before the finished product is obtained, the product loss is reduced, the method has the advantages of simple process and high yield, the yield of the salmizuril can reach 89.65%-94.81%, and the yield of the diclazuril can reach 80.20%-94.11%; and the problem of odor generation of decarboxylation reaction in the production process is also solved, and the method is beneficial to environmental protection and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of veterinary medicine, in particular to a preparation method of a triazone ring. Background technique [0002] Triazinone compounds, such as diclazuril and samizuril, are used to treat a variety of mammalian diseases caused by protozoa. Generally speaking, the mode of action of triazinone compounds is to attack intestinal wall cells and internal organs The intermediate stage of the parasite in the parietal cell, so that the endoplasmic reticulum surrounding the nucleus and mitochondria in the parasite cell expands, thereby interfering with the ability of the nucleus to divide, so that the schizont and microgametocyte remain in the young stage, and only a few Fewer merozoites and small gametes lead to the loss of the ability to penetrate new mammalian cells in the later parasitic stage, thereby effectively preventing the proliferation of parasites in the host. [0003] The application range of triazinones i...

AI Technical Summary

Problems solved by technology

However, this process is relatively complicated, the process cost is high and the yield is low, and a large amount of iron sludge is produced in the reduction section, which is not suitable for industrial production

[0005] Patent CN107746390 describes a method for synthesizing the triazone ring of diclazuril. The reduction product and ethyl malonyl dicarbamate undergo diazo, coupling, cyclization, hydrolysis, and decarboxylation reactions to generate the triazone ring of diclazuril. Although the oxazine ring solves the odor problem, there are a large number of filtration operations in the process, which also produces a large amount of waste residue, which is not conducive to clean production

[0006] Patent CN112457264 discloses a preparation method of samizuril, including using acetaminophen and 2-fluoro-5-nitrotoluene as starting materials, and realizing the triazone ring through coupling, cyclization, hydrolysis and decarboxylation However, this process uses a large amount of sodium hydroxide or potassium hydroxide to hydrolyze, and in the decarboxylation process, thioglycolic acid and other reagents with odor and environmental hazards are used, which brings serious environmental problems

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