Chemical synthesis method for 2-formylcyanoacetylhydrazone-quinoxaline-1,4-dioxide

A formyl cyanoacetyl hydrazone and dioxide technology, applied in the field of pharmaceutical synthesis, can solve the problems of harsh reaction conditions, difficult reaction control, severe reaction conditions and the like, and achieves short reaction route, low production cost and simple reaction equipment. Effect

Inactive Publication Date: 2010-11-03
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1) There are many reaction steps, there are 3 steps of reaction, and the resulting product yield is relatively low;
[0006] 2) The reagents and raw materials used are more expensive, and contain more toxic raw materials such as selenium dioxide and chromium trioxide;
[0007] 3) The post-processing of the reaction is troublesome, the pH value of the reaction solution needs to be adjusted, the reaction conditions are harsh, and the operation is difficult;
[0008] 4) The reaction conditions are severe, requiring reflux reaction, and the reaction is difficult to control;
[0009] 5) The production cost is relatively high

Method used

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  • Chemical synthesis method for 2-formylcyanoacetylhydrazone-quinoxaline-1,4-dioxide
  • Chemical synthesis method for 2-formylcyanoacetylhydrazone-quinoxaline-1,4-dioxide
  • Chemical synthesis method for 2-formylcyanoacetylhydrazone-quinoxaline-1,4-dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Accurately add 27.2 g (0.2 mol) of benzofurazan, 35 mL of N, N-dimethylformamide and aceguvaldehyde dimethyl acetal to a conventional 500 mL four-necked flask equipped with an electric stirrer, a thermometer and a dropping funnel 23.6g, stir to dissolve, when a clear and transparent solution is formed, slowly drop 3mL of pyrrolidine into the reaction with a dropping funnel, the whole reaction system is reacted at 5°C in the dark for 12h, after the reaction is completed, let it stand for 1h, and pump it under reduced pressure filter, wash the filter cake with 50 mL of methanol, and dry it in an oven at 70°C for 2 hours to obtain 23.6 g of quinoxaline-1,4-dioxo-2-carbaldehyde dimethyl acetal as light yellow solid powder, with a yield of 50%.

[0030] Accurately add 5.9 g (0.025 mol) of quinoxaline-1,4-dioxo-2-carbaldehyde dimethyl acetal to a conventional 500 mL four-necked flask equipped with an electric stirrer, a thermometer and a dropping funnel, add 90 mL of methanol ...

Embodiment 2

[0032] Accurately add 27.2 g (0.2 mol) of benzofuroxan, 45 mL of N, N-dimethylformamide and aceguvaldehyde dimethyl acetal to a conventional 500 mL four-necked flask equipped with an electric stirrer, a thermometer and a dropping funnel 47.2g, stir and dissolve, when a clear and transparent solution is formed, slowly drop 5mL of pyrrolidine into the reaction with a dropping funnel, the whole reaction system is reacted at 20°C in the dark for 20h, after the reaction is completed, let it stand for 1h, pump it under reduced pressure Filter, rinse the filter cake with 50 mL of methanol, and dry in an oven at 70° C. for 2 h to obtain 28.9 g of quinoxaline-1,4-dioxo-2-carbaldehyde dimethyl acetal as light yellow solid powder, with a yield of 62%.

[0033] Accurately add 5.9 g (0.025 mol) of quinoxaline-1,4-dioxo-2-carbaldehyde dimethyl acetal to a conventional 500 mL four-necked flask equipped with an electric stirrer, a thermometer and a dropping funnel, add methanol 125 mL and Con...

Embodiment 3

[0035] Accurately add 27.2 g (0.2 mol) of benzofuroxan, 60 mL of N, N-dimethylformamide and aceguvaldehyde dimethyl acetal to a conventional 500 mL four-neck flask equipped with an electric stirrer, a thermometer and a dropping funnel 82.6g, stirring and dissolving, when a clear and transparent solution is formed, slowly drop 5mL of pyrrolidine into the reaction with a dropping funnel, and the whole reaction system is reacted at 30°C in the dark for 24h. Filter, rinse the filter cake with 50 mL of methanol, and dry in an oven at 70°C for 2 hours to obtain 26.8 g of quinoxaline-1,4-dioxo-2-carbaldehyde dimethylacetal as a light yellow solid powder, with a yield of 57%.

[0036] Accurately add 5.9 g (0.025 mol) of quinoxaline-1,4-dioxo-2-carbaldehyde dimethyl acetal to a conventional 500 mL four-necked flask equipped with an electric stirrer, a thermometer and a dropping funnel, add 150 mL of methanol and Concentrated hydrochloric acid 110mL, carry out alcoholysis under the condit...

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Abstract

The invention belongs to the medicine synthesis field, in particular to a method for chemically synthesizing a feed additive 2-carbaldehyde acylhydrazone-quinoxaline-1,4-dioxide (cyadox). The invention comprises the steps that: benzofuroxan used as a raw material and N,N-dimethylformamide used as a reaction medium react with Methylglyoxal 1,1-dimethyl acetal under the function of catalyst pyrrolidine to synthesize an intermediate, quinoxaline-1,4-dioxygen-2-formaldehyde dimethyl acetal; the intermediate is alcoholysized in methanol and concentrated hydrochloric acid and reacts with cyanazine to synthesize the final product 2-carbaldehyde acylhydrazone-quinoxaline-1,4-dioxide (cyadox). The invention has the advantages of moderate reaction conditions, cheap and easily obtained raw material,low-toxicity or non-toxicity of all reagents, relatively high yield of synthesized product, relatively good purity and being applicable to expanded production under industrialization conditions.

Description

technical field [0001] The invention belongs to the field of medicine synthesis, and in particular relates to a chemical synthesis method of feed additive 2-formylcyanoacetylhydrazone-quinoxaline-1,4-dioxide (quinocedo). Background technique [0002] Quinoxaline-N, N-dioxine compounds are animal-specific drugs with broad-spectrum antibacterial and growth-promoting effects, and are widely used in the breeding industry. Representative varieties include carbadox and olaquindox. In recent years, it has been banned or restricted due to its obvious toxic side effects, and it is of great significance to develop such alternative products with lower toxic side effects. [0003] Quincedox is a new type of quinoxaline-N,N-dioxine compound, which has better antibacterial and growth-promoting effects. The clinical trial structure shows that both the general toxicity and specific toxicity are lower than similar drugs. Compared with other drugs of the same kind, cydox is more advanced an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/52A61P31/04
Inventor 袁宗辉邱荣超陶燕飞薛克友斯琴朝克图刘志亮王玉莲黄玲利陈冬梅彭大鹏戴梦红刘振利谢长清王旭
Owner HUAZHONG AGRI UNIV
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