Green synthesis method of anticoccidial veterinary drug Ethanamizuril

A green synthesis and anti-coccidian technology, applied in the direction of organic chemistry, can solve the problems of not being suitable for industrial production, limiting the application prospect of drugs, complicated post-processing procedures, etc., and achieve the effects of shortening the overall reaction steps, low cost, and cheap raw materials

Active Publication Date: 2020-04-03
SHANDONG GUOBANG PHARMA +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] But the synthetic method of prior art samizuril, its productive rate is low, and the whole reaction cost is big, and its reaction initial reaction product needs multi-step reaction just can make in addition, is equivalent to using conventional reagent production through nearly Only 10 multi-step reactions can synthesize samizuril, which requires a large investment and low yield, which also significantly increases the preparation cost, and the corresponding multi-step post-treatment process is complicated and produces a large amount of environmental pollutants
In addition, the most widely used preparation method of samizuril needs to go through ten steps of two-step hydrolysis, two-step reduction, neutralization, diazo coupling, cyclization, decarboxylation, condensation, and acylation, and the product quality is not good. , the color is reddish brown, the overall yield is only 32%, and the raw materials are rare and expensive, which is not suitable for industrial production, which greatly limits the application prospect of its drug itself

Method used

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  • Green synthesis method of anticoccidial veterinary drug Ethanamizuril
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  • Green synthesis method of anticoccidial veterinary drug Ethanamizuril

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Experimental program
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Effect test

Embodiment 1

[0037] The green synthesis method of the anticoccidial veterinary drug samizuril comprises the following steps:

[0038] Such as figure 1 and figure 2 As shown, step 1 diazo coupling reaction: In a 1000ml four-necked flask, add 215g of carboxylic acid protic solvent acetic acid, 43g of 4-chloro-3-methylaniline, and 97.19g of diethoxycarbonylmalonamide (EPC) 125.71g of 20% sodium nitrite aqueous solution was added dropwise, and the mol ratio of 4-chloro-3-methylaniline, diethoxycarbonyl malonamide (EPC) and sodium nitrite was 1:1.3:1.2; the diazo coupling reaction temperature At 5°C, carry out the diazo coupling reaction, heat the reaction for 10 hours until the reaction is complete, and obtain the diazo coupling compound (structure 1);

[0039] Such as image 3 As shown, the cyclization reaction of step 2: the diazo compound prepared in step 1 does not need to be separated, and 12.45 g of sodium acetate is directly added. The amount of sodium acetate added in the cyclizati...

Embodiment 2

[0044] The green synthesis method of the anticoccidial veterinary drug samizuril comprises the following steps:

[0045] Such as figure 1 and figure 2 As shown, step 1 diazo coupling reaction: In a 1000ml four-necked flask, add 215g of carboxylic acid protic solvent formic acid, 43g of 4-chloro-3-methylaniline, and 104.67g of diethoxycarbonyl malonamide (EPC) , drop 125.71g of 20% sodium nitrite aqueous solution, 4-chloro-3-methylaniline, diethoxycarbonyl malonamide (EPC) and sodium nitrite mol ratio are 1:1.4:1.2; Diazo coupling reaction temperature at 0°C, carry out the diazo coupling reaction, heat the reaction for 10 hours until the reaction is complete, and obtain the diazo coupling compound (structure 1);

[0046] Such as image 3 As shown, step 2 cyclization reaction: the diazo compound prepared in step 1 does not need to be separated, directly add 2.49 g of sodium acetate, the amount of sodium acetate added in the cyclization reaction and the 4-chloro-3 added in st...

Embodiment 3

[0051] The green synthesis method of the anticoccidial veterinary drug samizuril comprises the following steps:

[0052] Such as figure 1 and figure 2 As shown, step 1 diazo coupling reaction: In a 1000ml four-necked flask, add 215g of carboxylic acid protic solvent propionic acid, 43g of 4-chloro-3-methylaniline, 119.62g of diethoxycarbonyl malonamide (EPC) g. Add 157.14 g of 20% sodium nitrite aqueous solution dropwise, the molar ratio of 4-chloro-3-methylaniline, diethoxycarbonyl malonamide (EPC) and sodium nitrite is 1:1.6:1.5; diazo coupling reaction The temperature is 30°C, and the diazo coupling reaction is carried out, and the reaction is kept for 5 hours until the reaction is complete, and the diazo coupling compound (structure 1) is obtained;

[0053] Such as image 3 As shown, the cyclization reaction of step 2: the diazo compound prepared in step 1 does not need to be separated, and 12.45 g of sodium acetate is directly added. The amount of sodium acetate added...

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Abstract

The invention relates to a green synthesis method of anticoccidial veterinary drug Ethanamizuril, and solves the technical problems that in the prior art, an Ethanamizuril production method needs tensteps of reaction, the reaction steps are complex, the raw materials are difficult to obtain and high in price, the investment is large, the yield is low, the product quality is poor, the color is poor, and the method is not suitable for industrial production. According to the green synthesis method of anticoccidial veterinary drug Ethanamizuril, 4-chloro-3-methylaniline and EPC are taken as initial raw materials, diazo coupling, cyclization, hydrolysis, decarboxylation and condensation reaction are carried out to obtain the product Ethanamizuril. The method is widely applied to the technicalfield of veterinary drug synthesis.

Description

technical field [0001] The invention relates to the technical field of veterinary drug synthesis, in particular to a green synthesis method of the anticoccidial veterinary drug samizuril. Background technique [0002] Samizuril is a broad-spectrum anticoccidial drug with high efficiency and low toxicity. It can be used clinically for the control of poultry coccidiosis. Existing anticoccidial drugs such as toltrazuril and diclazuril are generally drug-resistant, and samizuril is a good substitute for anticoccidial drugs such as toltrazuril and diclazuril. more effective in pest control. [0003] Shamizuril is a new triazine anticoccidial drug independently developed by the Shanghai Veterinary Research Institute of the Chinese Academy of Agricultural Sciences (application number: 201310552795.2), which has no cross-resistance with diclazuril and toltrazuril, and Compared with Toltrazuril Clazuril, its anticoccidial effect is more obvious, without oocysts and lesions. Saliz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/075
CPCC07D253/075
Inventor 王兴国李琦斌乔建超娄燕昭
Owner SHANDONG GUOBANG PHARMA
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