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Preparation method of anticoccidial veterinary drug ethanamizuril

An anti-coccidial and sulfame technology, applied in the direction of organic chemistry and the like, can solve the problems of limited drug application prospects, unsuitable for industrial production, complicated post-processing procedures, etc., and achieves shortening the overall reaction steps, low cost, and high atomic utilization rate. Effect

Active Publication Date: 2020-04-17
SHANDONG GUOBANG PHARMA +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Preparation method of anticoccidial veterinary drug ethanamizuril

Examples

Experimental program
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Effect test

Embodiment 1

[0034] The method for preparing the anticoccidial veterinary drug samizuril comprises the following steps:

[0035] Such as figure 1 Shown, step 1 condensation reaction: in 250ml four-necked bottle, add organic solvent I DMF 120g, basic acid-binding agent sodium carbonate 26.33g, with 2-chloro-5-nitrotoluene 35.52g, acetaminophen 30g As a raw material, the mol ratio of paracetamol and 2-chloro-5-nitrotoluene is 1:1.05; the mol ratio of paracetamol and alkaline acid-binding agent is 1:1.2; Under the condition of 130°C, a condensation reaction occurs, and the reaction is kept for 5 hours until the reaction is complete, and then separated to obtain a condensation product (structure 1); the yield of this reaction is 90.20%.

[0036] Such as figure 2 As shown, step 2 reduction reaction: In a 250ml autoclave, add organic solvent II methanol 150g, condensation product (structure one) 50g in methanol, add Raney nickel catalyst 2.5g, condensation product in step 1 (structure one) T...

Embodiment 2

[0042] The method for preparing the anticoccidial veterinary drug samizuril comprises the following steps:

[0043] Such as figure 1 Shown, step 1 condensation reaction: in 250ml four-necked bottle, add organic solvent I DMSO 120g, basic acid-binding agent potassium carbonate 31.47g, with 2-chloro-5-nitrotoluene 35.52g, acetaminophen 30g As a raw material, the mol ratio of paracetamol and alkaline acid-binding agent is 1:1.1, and the mol ratio of paracetamol and 2-chloro-5-nitrotoluene is 1:1.05; Under the condition of 150°C, a condensation reaction occurs, and the reaction is kept for 4 hours until the reaction is complete, and then separated to obtain a condensation product (structure 1); the yield of this reaction is 91.50%.

[0044] Such as figure 2 As shown, step 2 reduction reaction: In a 250ml autoclave, add organic solvent II ethanol 150g, condensation product (structure one) 50g in methanol, add Raney nickel catalyst 2.0g, condensation product (structure one) and R...

Embodiment 3

[0050] The method for preparing the anticoccidial veterinary drug samizuril comprises the following steps:

[0051] Such as figure 1 As shown, step 1 condensation reaction: In a 250ml four-necked bottle, add organic solvent I DMAC120g, alkaline acid-binding agent sodium hydroxide 12.42g, 2-chloro-5-nitrotoluene 37.21g, paracetamol 30g As a raw material, the mol ratio of paracetamol and 2-chloro-5-nitrotoluene is 1:1.1; the mol ratio of paracetamol and alkaline acid-binding agent is 1:1.5; Under the condition of 140°C, a condensation reaction occurs, and the reaction is kept for 5 hours until the reaction is complete, and then separated to obtain a condensation product (structure 1); the yield of this reaction is 91.35%.

[0052] Such as figure 2 As shown, step 2 reduction reaction: In a 250ml autoclave, add organic solvent II toluene 150g, condensation product (structure one) 50g in methanol, add Raney nickel catalyst 10.0g, condensation product (structure one) and Raney T...

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Abstract

The invention relates to a preparation method of an anticoccidial veterinary drug ethanamizuril, and solves the technical problems that in the prior art, an ethanamizuril production method needs ten steps of reaction, the reaction steps are tedious, 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. The invention provides the preparation method of the anticoccidial veterinary drug samidazuril, wherein the preparation method comprises thefollowing steps: step 1, condensation reaction: in an organic solvent I, under the condition of an alkaline acid-binding agent, taking 2-chloro-5-nitrotoluene and acetaminophen as raw materials, carrying out condensation reaction, and separating to obtain a condensation product; step 2, reduction reaction; step 3, diazo coupling reaction; step 4, cyclization reaction; step 5, hydrolysis reaction;and 6, decarboxylation reaction to obtain the product samipril (structure 6). The method is widely applied to the technical field of veterinary drug synthesis.

Description

technical field [0001] The invention relates to the technical field of veterinary drug synthesis, in particular to a preparation 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. Salizuril...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/075
CPCC07D253/075
Inventor 王兴国刘聪乔建超安昌盛
Owner SHANDONG GUOBANG PHARMA
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