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Preparation method of cycloxaprid

A technology of cyclopyridin and chloromethylpyridine, which is applied in the direction of organic chemistry, can solve the problem that the yield is only 55%, and achieve the effect of ensuring the purity and safety of the preparation method

Inactive Publication Date: 2017-10-10
NANTONG TENDENCI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw material of this synthetic process is easy to get, easy to operate, mild reaction conditions, product content 97%, has industrial application prospect; %

Method used

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  • Preparation method of cycloxaprid
  • Preparation method of cycloxaprid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 100g concentrated sulfuric acid in 500ml round bottom flask, 50g guanidine nitrate is warmed up to 40 ℃ and reacts for 30min, puts into 400ml ice water and freezes and filters to obtain 68g nitroguanidine that the mass concentration percentage is 30% moisture; In 500ml round bottom flask Add 50g of solvent acetonitrile, 60g of paraformaldehyde, 68g of nitroguanidine containing 30% water in mass concentration, start stirring and heat up to 80°C, add 120g of 50% 2-chloro-5- Chloromethylpyridine solution, control the temperature not to exceed 80°C, slowly add 2-chloro-5-chloromethylpyridine dropwise, after the dropwise addition, control the temperature at 80°C and keep it warm for 10 hours, after the heat preservation, cool down to 10°C, Filter and dry to obtain cyclopyridin solid.

[0021] In this example, the content of cycloxaprid was analyzed by liquid chromatography to be 98.2%, and the molar yield of cyclopyrid was 95%.

Embodiment 2

[0023] Add 120g concentrated sulfuric acid in 500ml round bottom flask, 60g guanidine nitrate is heated up to 42 ℃ and reacts 40min, puts into 400ml ice water and freezes and filters to obtain the 81.6g nitroguanidine that contains mass concentration percentage and is 30% moisture; In 50ml round bottom flask Add 60g of solvent acetonitrile, 72g of paraformaldehyde, 81.6g of nitroguanidine containing 30% moisture in mass concentration, start stirring and heat up to 85°C, add 127g of 50% 2-chloro- 5-chloromethylpyridine solution, control the temperature not to exceed 85°C, slowly add 2-chloro-5-chloromethylpyridine dropwise, after the dropwise addition, control the temperature at 85°C for 8 hours, and cool down to 10 °C, filtered, and dried to obtain cyclopyridin as a solid.

[0024] In this example, the content of cycloxaprid was analyzed by liquid chromatography to be 98.6%, and the molar yield of cyclopyrid was 95.2%.

Embodiment 3

[0026] Add 100g concentrated sulfuric acid in 500ml round bottom flask, 50g guanidine nitrate is warmed up to 41 ℃ and reacts for 30min, put into 400ml ice water and freeze and filter to obtain 68g nitroguanidine that the mass concentration percentage is 30% moisture; In 500ml round bottom flask Add 50g of solvent acetonitrile, 60g of paraformaldehyde, 68g of nitroguanidine containing 30% water in mass concentration, start stirring and heat up to 80°C, add 120g of 50% 2-chloro-5- Chloromethylpyridine solution, control the temperature not to exceed 80°C, slowly add 2-chloro-5-chloromethylpyridine dropwise, after the dropwise addition, control the temperature at 85°C for 9 hours, and after the heat preservation, cool down to 10°C, Filter and dry to obtain cyclopyridin solid.

[0027] In this example, the content of cycloxaprid was analyzed by liquid chromatography to be 98.8%, and the molar yield of cyclopyrid was 95.6%.

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Abstract

The invention relates to a preparation method of cycloxaprid. The preparation method comprises steps as follows: (1), concentrated sulfuric acid is added to a reaction kettle A, guanidine nitrate is added, and the mixture is heated to 40-42 DEG C and reacts for 30-40 min; (2), after the reaction, nitroguanidine as an intermediate is obtained through ice hydrolysis, cooling and filtering; (3), acetonitrile as a solvent, paraformaldehyde and nitroguanidine obtained in the step (2) are added to a reaction kettle B in sequence, stirred uniformly and heated to 80-85 DEG C, 2-chloro-5-chloromethylpyridine is dropwise added to a reaction system slowly, and the temperature is controlled to be lower than or equal to 80 DEG C; (4), after 2-chloro-5-chloromethylpyridine is dropwise added, the temperature is preserved for 8-10 h under a temperature system lower than or equal to 80 DEG C; (5), after the reaction, cooling is performed, solids are filtered out, and cycloxaprid is obtained after drying. The preparation method of cycloxaprid has the advantages as follows: purity of the cycloxaprid product can be guaranteed, and yield of the cycloxaprid product can be increased.

Description

technical field [0001] The invention belongs to the technical field of insecticide preparation, in particular to a preparation method of cyclopyrid. Background technique [0002] Cyclopyrid, as a new type of neonicotinoid insecticide, has a unique mechanism of action. It is the only insecticide found to have an obvious antagonistic effect on insect nicotinic acetylcholine receptors. Sexual pests have significant activity, and also have a good control effect on Lepidoptera pests, and it is expected to become a neonicotinoid insecticide with strong market competitiveness. [0003] After searching, there are currently existing literatures disclosing the synthesis process of cyclopyrid, using nitroethylene dichloride as raw material, firstly obtaining dimethoxynitroethylene through nitration, and then synthesizing nitromethyleneimidazolidine through ring closure reaction , and then the important intermediate chlorpyridine nitromethyleneimidazolidine was obtained through condens...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/18
CPCC07D498/18
Inventor 洪飞金标
Owner NANTONG TENDENCI CHEM
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