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Synthesis method of pesticide sulfoxaflor intermediate 3-[1-(methylthio)ethyl]-6(trifluoromethyl)pyridine

A technology of trifluoromethylpyridine and sulfenalazine, which is applied in the field of pesticide pharmacy, can solve problems such as long reaction steps, and achieve the effects of short steps, few side reactions and high reaction yield

Inactive Publication Date: 2018-12-21
SHANDONG ACADEMY OF PESTICIDE SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has the disadvantage of long reaction steps

Method used

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  • Synthesis method of pesticide sulfoxaflor intermediate 3-[1-(methylthio)ethyl]-6(trifluoromethyl)pyridine
  • Synthesis method of pesticide sulfoxaflor intermediate 3-[1-(methylthio)ethyl]-6(trifluoromethyl)pyridine
  • Synthesis method of pesticide sulfoxaflor intermediate 3-[1-(methylthio)ethyl]-6(trifluoromethyl)pyridine

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Embodiment 1

[0032] The synthetic method of 3-[1-(methylthio) ethyl]-6 (trifluoromethyl) pyridine may further comprise the steps:

[0033] 1) Under the protection of argon, mix methyl ethyl sulfide, nitrobenzene, catalyst and triethylamine, raise the temperature to 125°C, control the pressure to 2.5 atmospheres, add dropwise 1mol of 5-bromo-2- The mixture of trifluoromethylpyridine and toluene was controlled to be dropped in 40 minutes, the reaction temperature was controlled to be 149° C., the reaction pressure was 6 atmospheres, and the reaction was continued for 14 hours to complete.

[0034] Among them, the catalyst is a solid base, and the preparation process is as follows: calcium oxide, zinc oxide and aluminum oxide are mixed according to the material ratio of 1:0.91:1.18, and then ground, and 800-mesh particles are taken, and roasted at 800 ° C for 17 hours to obtain the catalyst.

[0035] The molar ratio of 5-bromo-2-trifluoromethylpyridine, methyl ethyl sulfide and triethylamine ...

Embodiment 2

[0038] The synthetic method of 3-[1-(methylthio) ethyl]-6 (trifluoromethyl) pyridine may further comprise the steps:

[0039] 1) Under the protection of nitrogen, mix methyl ethyl sulfide, toluene, catalyst and ethylenediamine, raise the temperature to 110°C, control the pressure to 2 atmospheres, and drop 1mol of 5-chloro-2-trifluoroform The mixture of pyridine and benzene was controlled to be dripped in 30 minutes, the reaction temperature was controlled to be 140° C., the reaction pressure was 4 atmospheres, and the reaction was continued for 10 hours to complete.

[0040] Among them, the catalyst is a solid base, and the preparation process is as follows: calcium oxide, zinc oxide and aluminum oxide are mixed according to the material ratio of 1:0.8:1.12, and then ground, and 500-mesh particles are taken, and roasted at 750 ° C for 12 hours to obtain the catalyst.

[0041] The molar ratio of 5-chloro-2-trifluoromethylpyridine, methyl ethyl sulfide and ethylenediamine is 1:...

Embodiment 3

[0044] The synthetic method of 3-[1-(methylthio) ethyl]-6 (trifluoromethyl) pyridine may further comprise the steps:

[0045] 1) Under the protection of argon, mix methyl ethyl sulfide, xylene, catalyst and triethylamine, raise the temperature to 135°C, control the pressure to 3 atmospheres, add dropwise 1mol of 5-iodo-2-tris The mixture of fluoromethylpyridine and toluene was controlled to be dropped in 45 minutes, the reaction temperature was controlled to be 155° C., the reaction pressure was 7 atmospheres, and the reaction was continued for 15 hours to complete.

[0046] Among them, the catalyst is a solid base, and the preparation process is as follows: calcium oxide, zinc oxide and aluminum oxide are mixed according to the material ratio of 1:0.96:1.25, and then ground, and 650-mesh particles are taken, and roasted at 780 ° C for 15 hours to obtain the catalyst.

[0047]The molar ratio of 5-iodo-2-trifluoromethylpyridine, methyl ethyl sulfide and triethylamine is 1:2.2:1...

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Abstract

The invention discloses a synthesis method of a pesticide sulfoxaflor intermediate 3-[1-(methylthio)ethyl]-6(trifluoromethyl)pyridine, and belongs to the field of pesticide preparation. The synthesismethod is characterized in that a reaction is performed on 5-halo-2-trifluoromethylpyridine and methyl ethyl sulfide under the action of a catalyst to obtain the 3-[1-(methylthio)ethyl]-6(trifluoromethyl)pyridine. A reaction process comprises the following steps: 1), under a protective gas condition, uniformly mixing the methyl ethyl sulfide, a solvent A, the catalyst and an acid binding agent, raising the temperature to 110-135 DEG C, controlling the pressure to be 2-3 atmospheric pressures, dropwise adding a mixture of the 5-halo-2-trifluoromethylpyridine and a solvent B within 30-45 min, controlling the reaction temperature to be 140-155 DEG C, controlling the reaction pressure to be 4-7 atmospheric pressures, and continuing the reaction for 10-15 hours; 2), cooling a system, filteringto remove an insoluble matter to obtain a filtrate, adding the filtrate into an about 2-3-fold saturated saline solution by volume, allowing standing still for layering, washing an organic phase by using water, then drying with a drying agent, and then concentrating to obtain the 3-[1-(methylthio)ethyl]-6(trifluoromethyl)pyridine. By the synthesis method, the steps are few, the yield is relativelyhigh and the pollutant emission is less.

Description

technical field [0001] The invention belongs to the field of pesticide pharmacy, and in particular relates to a method for synthesizing the insecticide sulfoxaflor intermediate 3-[1-(methylthio)ethyl]-6(trifluoromethyl)pyridine. Background technique [0002] Sulfoxaflor (sulfoxaflor) developed the first novel sulfoximine agricultural insecticide for Dow AgroSciences. On November 2, 2010, the World Pesticide Research Conference was held in London, England. The company will its publication. The insecticidal spectrum of sulfoxaflor is different from that of neonicotinoid insecticides. It also has a high control effect on piercing and sucking insects that are resistant to neonicotinoids. It can be said that it is a key point in resistance management. The new control agent was recognized by the Insecticide Resistance Action Committee (IRAC) as the only member of the new Group 4C class of insecticides. The molecular formula of sulfoxaflor is C 10 h 10 f 3 N 3 OS, the chemica...

Claims

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Application Information

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IPC IPC(8): C07D213/32
Inventor 杨朝晖付洪信王玲
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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