Preparation method of 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one

A technology of difluoromethyl and dichlorophenyl, applied in the field of chemical preparation, can solve the problems of complex treatment process, unfavorable environmental protection, excessive waste water, etc., achieves cheap and easy-to-obtain process raw materials, is conducive to environmental protection treatment, and simplifies the process effect of operation

Pending Publication Date: 2020-09-22
湖南斯派克科技股份有限公司
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Problems solved by technology

[0011] The invention provides a preparation method of 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazol-5-one, to solve The raw materials for the preparation of 1-(2,4-dichlorophenyl)-4-difluorome

Method used

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  • Preparation method of 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one

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Example Embodiment

[0036] Example 1

[0037] Preparation of catalyst X: Dissolve 3.72g (0.0196mol) of tin dichloride and 0.057g (0.0004mol) of germanium dichloride in 20g of water with a pH of 3 at room temperature.

[0038] Step 1. Mix 93.1g (1mol) of aniline a with 148g (1.5mol) of 37% concentrated hydrochloric acid to form an aniline hydrochloride solution, cool to 0°C and add 207g (1.2mol) of 40% sodium nitrite solution dropwise, Add all the prepared catalyst X solution dropwise at 0-5°C, react at room temperature for 6 hours, and adjust the pH value of the reaction solution to 11-12 with 30% sodium hydroxide solution. Add 186.2g tert-butanol, add 104.7g (0.95mol) 40% acetaldehyde aqueous solution dropwise at 0-5℃, add 65g (1mol) sodium cyanate, after the reaction solution is clear, add 60.1g (1mol) acetic acid dropwise, below room temperature Stir for 3h, drop the temperature to 0-5℃ and add 706.8g (0.95mol) 10% sodium hypochlorite solution dropwise, stir for 2h, filter, wash the filter cake wi...

Example Embodiment

[0043] Example 2

[0044] The preparation of catalyst X, step 1, preparation of catalyst Y, preparation of catalyst Z, and step 3 were the same as in Example 1.

[0045] Wherein step 2 is: put 151.8g (0.85mol) 1-phenyl-3-methyl-1H-1,2,4-triazol-5-one b and 2.5g of the catalyst Y into 203.6g acetonitrile, Replace the air in the reaction system with nitrogen, stir and raise the temperature to 60℃, and pass in 110.7g (1.28mol) of monochlorodifluoromethane within 5h, then filter after cooling to room temperature, and wash the filter with 151.8g of ethylene glycol monomethyl ether Cake, combine the filtrate and desolvate to obtain 187g of reddish brown solid, 1-phenyl-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5-one c content of 95.2% , The yield is 93.1% based on 1-phenyl-3-methyl-1H-1,2,4-triazol-5-one b.

Example Embodiment

[0046] Example 3

[0047] The preparation of catalyst X, step 1, the preparation of catalyst Z, and step 3 were the same as in Example 1.

[0048] The catalyst Y was prepared as follows: 10.7g (0.255mol) sodium fluoride and 10.7g diatomaceous earth (325 mesh, specific surface area 600m 2 / g) Put into 21.4g water, stir evenly, remove water by rotary evaporation, vacuum dry, and set aside.

[0049] Step 2 is to put 151.8g (0.85mol) 1-phenyl-3-methyl-1H-1,2,4-triazol-5-one b and the catalyst Y2g into 203.6g acetonitrile, and then replace with nitrogen The air in the reaction system was stirred and heated to 60°C. 88.2g (1.02mol) of monochlorodifluoromethane was introduced within 5h, and filtered after being cooled to room temperature. The filter cake was washed with 152g of ethylene glycol monomethyl ether, and the filtrate was combined. After desolvation, 187 g of a reddish brown solid was obtained. The content of 1-phenyl-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5-one c was 95.1%, ...

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Abstract

The invention provides a preparation method of 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one. The method comprises the steps: taking aniline as a raw material; reducing witha catalyst X to prepare phenylhydrazine; under the action of acetaldehyde and sodium cyanate, carrying out cyclization on phenylhydrazine to generate 1-phenyl-3-methyl-1H-1,2,4-triazole-5-one; carrying out a reaction on 1-phenyl-3-methyl-1H-1,2,4-triazole-5-one and monochlorodifluoromethane under the action of a catalyst Y to generate 1-phenyl-3-methyl-4-difluoromethyl-1H-1,2,4-triazole-5-one, and carrying out catalytic chlorination through a catalyst Z to prepare 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one.

Description

technical field [0001] The invention belongs to the technical field of chemical preparation, in particular to a pesticide sulfentrazone intermediate 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2, Process for the preparation of 4-triazol-5-one. Background technique [0002] Sulfentrazone was developed by FMC and launched in 1996 for the control of broad-leaved weeds in soybean fields, 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H- 1,2,4-triazol-5-one is an intermediate for the preparation of the pesticide sulfentrazone, and there are many synthetic methods. [0003] The compound sulfentrazone structure was first reported by U.S. Patent US4818275, and US4909831 disclosed that 2,4-dichlorophenylhydrazine was used as a starting material, and 2-oxopropionic acid, triethylamine, diphenylphosphoric azide and a Chlorodifluoromethane and the like are used to prepare the intermediate and sulfentrazone, but the raw materials are expensive and the cost is relatively hi...

Claims

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Application Information

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IPC IPC(8): C07D249/12B01J27/135B01J27/12B01J27/125
CPCC07D249/12B01J27/135B01J27/125B01J27/10B01J21/16B01J27/12B01J35/0006
Inventor 段相生王洪成徐小飞彭宇新伍先辉蒋泽平
Owner 湖南斯派克科技股份有限公司
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