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Synthetic process of fluazinam

A synthesis process, the technology of fluazinam, applied in the field of synthesis process of fluazinam, can solve the problems of high post-treatment purification pressure, unfavorable industrial production, and unit consumption cost of nitrates, so as to save purification steps and reduce nitrates Unit consumption, the effect of reducing production costs

Active Publication Date: 2019-08-20
DALIAN JOIN KING FINE CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this process, after the reaction liquid after ammonia amination is filtered to remove inorganic salts, a certain amount of ammonia gas is still dissolved in the system, and the next step of condensation reaction is directly carried out, and ammonia gas will also have side reactions with nitrates to generate 2 -Chloro-3,5-dinitro-4-amino-benzotrifluoride and 2,4-diamino-3,5-dinitro-benzotrifluoride, resulting in high unit consumption of nitrates and high cost, crude Low product purity and high post-treatment purification pressure are not conducive to industrial production

Method used

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  • Synthetic process of fluazinam
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  • Synthetic process of fluazinam

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 51.2 g (0.2348 mol, 99%, 1.0 eq) of 2,3-dichloro-5-trifluoromethylpyridine and 160 mL of tetrahydrofuran were put into a 500 mL autoclave, and the autoclave was closed. Nitrogen was replaced three times at room temperature, 20.0 g (1.174 mol, 5.0 eq) of liquid ammonia was passed into the system, and the internal pressure of the system was about 0.6 Mpa. Raise the temperature to 100°C and hold the pressure for 28 hours. The pressure of the system drops from 1.6Mpa to 1.2Mpa. The reaction of the raw materials controlled by HPLC is completed by inserting a bottom tube to sample. After the system was lowered to normal temperature, the pressure was released to normal pressure, and the released ammonia gas was absorbed with tetrahydrofuran. The reaction solution was taken out, filtered, and rinsed with an appropriate amount of tetrahydrofuran, and the mother liquor was subjected to deamination treatment in the next step.

[0027] The above mother liquor was transferred into ...

Embodiment 2

[0033]47.3 g (0.2348 mol, 99%, 1.0 eq) of 2-fluoro-3-chloro-5-trifluoromethylpyridine and 120 mL of THF were put into a 500 mL autoclave, and the autoclave was closed. Nitrogen was replaced three times, 12.0 g (0.7044 mol, 3.0 eq) of liquid ammonia was passed into the system, and the pressure in the system was about 0.5 Mpa. Raise the temperature to 30°C and hold the pressure for 25 hours. The pressure of the system drops from 0.9 Mpa to 0.7 Mpa. The reaction of the raw materials controlled by HPLC is completed by inserting a bottom tube for sampling. After the system was lowered to normal temperature, the pressure was released to normal pressure, and the released ammonia gas was absorbed with tetrahydrofuran. The reaction solution was taken out, filtered, and the mother liquor was subjected to the next step of deamination treatment.

[0034] Transfer the above mother liquor into a 1000mL four-necked bottle, and remove the ammonia gas under reduced pressure at 10-15°C for 2 h...

Embodiment 3

[0040] 51.2 g (0.2348 mol, 99%, 1.0 eq) of 2,3-dichloro-5-trifluoromethylpyridine and 200 mL of tetrahydrofuran were put into a 500 mL autoclave, and the autoclave was closed. Nitrogen was replaced three times, 40.0 g (2.348 mol, 10.0 eq) of liquid ammonia was passed into the system, and the pressure in the system was about 0.7 Mpa. Raise the temperature to 70°C and hold the pressure for 32 hours. The pressure of the system drops from 1.6 Mpa to 1.2 Mpa, and the reaction of the raw materials controlled in the sampling process is complete. After the system was lowered to normal temperature, the pressure was released to normal pressure, and the released ammonia gas was absorbed with tetrahydrofuran. The reaction solution was taken out, filtered, and the mother liquor was subjected to the next step of deamination treatment.

[0041] The mother liquor was transferred into a 1000 mL four-necked bottle, cooled to -10°C in an ice-salt bath for 3 hours to remove ammonia under reduced...

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Abstract

The invention discloses a synthetic process of fluazinam, and belongs to the technical field of pesticide chemical engineering. The process comprises the following steps: taking 2-halogen-3-chloro-5-trifluoromethyl pyridine and ammonia gas as raw materials to carry out an amination reaction in an ether solvent in a high-pressure kettle, carrying out desalination and deamination on the reaction liquid, then carrying out a condensation reaction with 2,4-dichloro-3,5-binitro-trifluorotoluene under an alkaline condition, and carrying out a conventional post-treatment method to obtain the fluazinam. According to the invention, in a continuous process of the two-step process, generation of side reactions of 2,4-dichloro-3,5-binitro-trifluorotoluene during the condensation reaction due to ammoniaresidues in an amine solution is avoided, so that unit consumption of the 2,4-dichloro-3,5-binitro-trifluorotoluene is reduced to a stoichiometric ratio, and product purification and yield are greatly improved. The product does not need to be purified, the purity can reach 99% or above, and the total separation yield of two steps can reach 97% or above.

Description

technical field [0001] The invention relates to the technical field of pesticide chemical industry, in particular to a synthesis process of fluazinam. Background technique [0002] Fluazinam, whose chemical name is N-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-3-chloro-4-(trifluoromethyl)-2,6- Dinitroaniline is a broad-spectrum and highly effective protective fungicide of dinitroanilines launched by Ishihara Co., Ltd. in Japan in 1988. Scrubs are very effective. Fluazinam is the only mitochondrial oxidative phosphorylation uncoupler with no cross-resistance to existing agents. By acting on ATP synthase, it releases the association between oxidation and phosphorylation at the end of the respiratory chain, maximally consumes the electrochemical potential energy accumulated by electron transfer, and its sterilization speed and activity are ahead of similar compounds. Fluazinam has multiple action sites on ATP synthase, controlled by multiple genes, and the risk of resistance is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74
CPCC07D213/74
Inventor 王荣良王俊春
Owner DALIAN JOIN KING FINE CHEM CO LTD
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