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Synthesis method of prothioconazole

A synthesis method and technology of prothioconazole, applied in the field of organic synthesis, can solve the problems of large amount of oxidant, many impurities in the final product, complicated operation and the like

Pending Publication Date: 2022-05-13
LIAONING ZHONGHUI BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the currently reported synthetic processes for prothioconazole have problems such as large material consumption, large amount of waste water, large amount of solid waste, low yield, and poor process fluency.
For example, in the synthetic route of US6559317, when prothioconazole was prepared from compound 1, an excessive amount of ferric chloride was used as a reaction reagent, resulting in a large amount of solid waste generated by the reaction
CN108689952A uses ferric chloride as an oxidizing agent, and after the reaction is completed, the water phase needs to be oxidized with hydrogen peroxide before it can be reused. The operation is cumbersome and the process fluency is relatively poor
CN106986838A uses hydrogen peroxide or m-chloroperoxybenzoic acid as oxidant, and this method consumes a large amount of oxidant
And after repeated tests and verifications by the inventor, it was found that the final product obtained by this method has more impurities and a very low yield, and the product obtained by the reaction has a high viscosity, which makes separation and purification very difficult
CN109912522 uses nitric acid as an oxidizing agent, and nitric acid is an explosive product, and participating in chemical reactions has great safety risks

Method used

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  • Synthesis method of prothioconazole
  • Synthesis method of prothioconazole
  • Synthesis method of prothioconazole

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preparation example Construction

[0035] The synthetic method of described kind of high-yield prothioconazole and aftertreatment thereof, comprises the following steps:

[0036] 1) Add compound 1 to the solvent, add a certain amount of titanium-silicon molecular sieve, add a certain amount of hydrogen peroxide dropwise at a certain temperature, keep warm for a period of time after the addition is completed, and monitor the raw material within 1% by liquid chromatography; Filtrate, recover the catalyst titanium-silicon molecular sieve and apply mechanically, the filtrate is allowed to stand and separate into layers to separate the water phase, and the organic phase is precipitated to obtain the product prothioconazole;

[0037] Apply titanium silicate molecular sieve steps:

[0038] 2) Add compound 1 into the solvent, add recovered titanium-silicon molecular sieve, add a certain amount of hydrogen peroxide dropwise under certain temperature conditions, keep warm for a period of time after the addition is comple...

Embodiment 1

[0053] Compound 1,2-(1-chloro-cyclopropan-1-yl)-1-(2-chlorophenyl)-2-hydroxyl-3-(1,2,4-triazolidine-5-thione -1-yl)-propane (69.2g, 0.2mol) was added to 210g toluene, 2.07g of titanium silicon molecular sieve was added, the temperature was raised to 40°C, 10% hydrogen peroxide (68.0g, 0.2mmol) was added dropwise, and the temperature of the reaction solution was controlled to 40- 45°C, after the dropwise addition is completed, keep at 40°C for 3 hours. After the reaction, the temperature was lowered to 25°C, the titanium silicon molecular sieve was recovered by filtration, the filtrate was allowed to stand for stratification, and the organic phase was desolvated to obtain a white solid, namely 68.0 g of prothioconazole, with a content of 98.4% and a yield of 97.3%.

[0054] The nuclear magnetic data of gained product is: 1 HNMR (600MHz, DMSO-d 6 ) δ (ppm) 13.67 (lH, s), 8.43 (lH, s), 7.53-7.55 (lH, m), 7.37-7.39 (lH, m), 7.21-7.26 (2H, m), 5.06 (lH, s), 4.48(2H, s), 3.34(lH,...

Embodiment 2

[0057] Compound 1,2-(1-chloro-cyclopropan-1-yl)-1-(2-chlorophenyl)-2-hydroxyl-3-(1,2,4-triazolidine-5-thione -1-yl)-propane (69.2g, 0.2mol) was added to 180g dichloroethane, 2.07g titanium silicon molecular sieve was added, the temperature was raised to 40°C, 10% hydrogen peroxide (68.0g, 0.2mmol) was added dropwise, and the reaction solution was controlled The temperature is 40-45°C, and the temperature is kept at 40°C for 3 hours after the dropwise addition is completed. After the reaction, the temperature was lowered to 25°C, the titanium silicon molecular sieve was recovered by filtration, the filtrate was allowed to stand for stratification, and the organic phase was desolvated to obtain a white solid, which was prothioconazole 67.9g, with a content of 98.4%, and a yield of 97.2%.

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Abstract

The invention discloses a method for preparing prothioconazole with high yield, which comprises the following steps of: reacting a compound 1 at 0-100 DEG C in the presence of hydrogen peroxide and a solvent by taking a titanium silicalite molecular sieve as a catalyst, filtering and recovering the catalyst after the reaction is finished, and performing post-treatment to obtain the prothioconazole. The method is simple to operate, smooth in process, mild in condition, green and environment-friendly, good in atom economy, high in raw material conversion rate and high in product yield, and the catalyst can be repeatedly utilized for multiple times. And the method has very high industrial production value.

Description

technical field [0001] The present invention relates to the field of organic synthesis. Specifically, the present invention relates to a method for synthesizing prothioconazole with high yield. Background technique [0002] The chemical name of prothioconazole is 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-3H-1, 2,4-triazole-3-thione, which is a demethylation inhibitor (DMIs) developed by Bayer, its mechanism of action is to inhibit the 14-position demethylation of lanosterol, the precursor of true middle sterol It has the advantages of wide bactericidal spectrum, good systemic activity, high protection, treatment and eradication activity, and long validity period. Through a large number of field efficacy tests, the results show that prothioconazole not only has good safety for crops, but also has obvious effects in disease prevention and treatment, and has a good effect in increasing production. Prothioconazole is mainly used to prevent and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 郭建法王涛孔前广韩海平方燕董建生
Owner LIAONING ZHONGHUI BIOTECHNOLOGY CO LTD
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