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Synthesis method for 2-formylcarbonylhydrazone-sulfaquinoxaline-N1, N4-dioxide

A technology of formylformylhydrazone and methylquinoxaline, which is applied in the field of preparation of 2-formylformylhydrazone-quinoxaline-N1,N4-dioxide, can solve the problems of few literature reports and achieve The synthesis steps are simple, the post-processing is convenient, and the effect of high purity

Inactive Publication Date: 2013-05-01
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no patent on the synthesis of 2-formylformylhydrazone-quinoxaline-N1,N4-dioxide at home and abroad, and there are few literature reports. In order to fill this gap, further confirm its generation, and study its toxicity Side effects, it is very important to prepare 2-formylformylhydrazone-quinoxaline-N1,N4-dioxide by chemical synthesis method for comparison, and 2-formylformylhydrazone-quinoxaline-N1,N4-dioxide The chemical synthesis of oxides can not only provide standard products for the residue and metabolism of such drugs, but also provide reference methods for similar metabolites

Method used

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  • Synthesis method for 2-formylcarbonylhydrazone-sulfaquinoxaline-N1, N4-dioxide
  • Synthesis method for 2-formylcarbonylhydrazone-sulfaquinoxaline-N1, N4-dioxide
  • Synthesis method for 2-formylcarbonylhydrazone-sulfaquinoxaline-N1, N4-dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Synthesis of 2-methylquinoxaline-N1, N4-dioxide

[0029] Add benzofurazan (26.3g) in acetone (14g), K 2 CO 3 (50g), CH 2 Cl 2 (200ml), drop n-butylamine (28.2g) within 1h at 30°C under stirring, continue stirring for 5h, filter off K 2 CO 3 , concentrated by distillation under reduced pressure, added isopropanol, and placed in ice water to precipitate out the precipitate. After filtration, 40 g of a yellow solid containing a small amount of benzofurazan was obtained, which was recrystallized several times from ethanol to obtain 31 g of yellow needle crystals, 2-methylquinoxaline-N1, N4-dioxide. When the temperature of the reaction system exceeds 60°C, explosion will occur.

[0030] (2) Synthesis of 2-formyl-quinoxaline-N1, N4-dioxide

[0031] 13g of 2-methylquinoxaline-N1,N4-dioxide was placed in a reaction flask, dissolved in 100ml of tetrahydrofuran, and heated to 70°C. Take 8.5g of selenium dioxide, stir and dissolve it with 60ml of tetrahydrofuran and 5....

Embodiment 2

[0038] (1) Synthesis of 2-methylquinoxaline-N1, N4-dioxide

[0039] Add benzofurazan (30g) in acetone (15g), K 2 CO 3 (56g), CHCl 3 (200ml), under stirring, drop n-butylamine (30g) at 20°C within 1h, continue stirring for 6h, and filter off K 2 CO 3 , concentrated by distillation under reduced pressure, added isopropanol, and placed in ice water to precipitate out the precipitate. After filtration, 40 g of a yellow solid containing a small amount of benzofurazan was obtained, and 32 g of yellow needle-like crystals were obtained by recrystallization from ethanol several times. When the temperature of the reaction system exceeds 60°C, explosion will occur.

[0040] (2) Synthesis of 2-formyl-quinoxaline-N1, N4-dioxide

[0041]Take 13g of 2-methylquinoxaline-N1,N4-dioxide in a reaction flask, dissolve it in 100ml of tetrahydrofuran, and heat to 70°C. Take 7.8g of selenium dioxide, stir and dissolve it with 60ml of tetrahydrofuran and 5.9ml of water, and add it dropwise int...

Embodiment 3

[0047] (1) Synthesis of 2-methylquinoxaline-N1, N4-dioxide

[0048] Add benzofurazan (31g) in acetone (15g), K 2 CO 3 (60g), CH 2 Cl 2 (200ml), drop n-butylamine (33g) within 1h at 50°C under stirring, continue stirring for 5h, filter off K 2 CO 3 , concentrated by distillation under reduced pressure, added isopropanol, and placed in ice water to precipitate out the precipitate. After filtration, 40 g of a yellow solid containing a small amount of benzofurazan was obtained, which was recrystallized several times from ethanol to obtain 33 g of yellow needle-like crystals. When the temperature of the reaction system exceeds 60°C, explosion will occur.

[0049] (2) Synthesis of 2-formyl-quinoxaline-N1, N4-dioxide

[0050] 13 g of 2-methylquinoxaline-N1, N4-dioxide was placed in a reaction flask, dissolved in 100 ml of dioxane, and heated to 70°C. Take 9.1g of selenium dioxide, stir and dissolve it with 60ml of tetrahydrofuran and 5.9ml of water, and add it dropwise into t...

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Abstract

The invention discloses a synthesis method for 2-formylcarbonylhydrazone-sulfaquinoxaline-N1, N4-dioxide in the technical field of biochemical engineering. The invention discloses a structure of a sulfaquinoxaline drug metabolite, a preparation method for the structure and application of the structure. The sulfaquinoxaline drug metabolite is the 2-formylcarbonylhydrazone-sulfaquinoxaline-N1, N4-dioxide, and the molecular formula of the sulfaquinoxaline drug metabolite is C10H8N4O3. The synthesis method disclosed by the invention comprises the following steps of: performing ring expansion, oxidation and aldol condensation to obtain a 2-formylcarbonylhydrazone-sulfaquinoxaline-N1, N4-dioxide crude product by taking benzofurazan and ethyl formate as raw materials, and performing recrystallization and purification on the crude product for three times to obtain a product with higher purity. According to the synthesis method, a common solvent which can be simply and easily obtained is adopted to serve as a reaction medium; a used instrument and the reaction condition also can be easily implemented; synthesis steps are fewer; postprocessing is convenient; and the obtained product is higher in purity.

Description

technical field [0001] The invention belongs to the technical field of biochemical industry, and in particular relates to a preparation method of 2-formylformylhydrazone-quinoxaline-N1,N4-dioxide. Background technique [0002] Quinoxaline drugs are quinoxaline-N 1 , N 4 - A class of chemically synthesized animal-specific drugs with antibacterial and growth-promoting effects based on the basic structure of dioxide, mainly including a class of new veterinary drugs quinocetone and cydox with independent intellectual property rights in my country. At present, the safety of quinoxaline drugs is a hot spot in food safety, and veterinary drug residues in animal products can cause harm to human health and directly hinder the development of the industry. Therefore, the Laboratory of Veterinary Drug Metabolism is an important scientific and technological problem that should be solved to avoid veterinary drug residues. When studying the metabolic pathway of this type of drug, it was ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/52
Inventor 高海翔李松卿张素霞
Owner CHINA AGRI UNIV
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