Method for preparing herbicide flufenacet intermediate tda-sulfone

A synthetic method, thiadiazole technology, applied in the direction of organic chemistry, can solve problems such as difficult to remove, uncontrollable safety, long reaction time, etc., to increase the service life of equipment, avoid large amounts of aggregation, and improve the intrinsic safety of the process Effect

Active Publication Date: 2019-01-11
SHANGHAI LINKCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But there are many defects in the prior art, for example, there is 2-methylsulfoxide by-product 2-methylsulfoxide-5-trifluoromethyl-1,3,4-thiadiazole (formula 2) in the reaction, and it is difficult to Difficult to remove; longer reaction time (for example, U.S. Patent US6031108 (Example 1), the method reported requires more than 11 hours; Li Yusheng, Zhou Guidong, Shen Yiquan, etc., the synthesis of flufenacet, "Modern Pesticides", 2002 Year, No. 2, P8-10, the reported method takes more than 9 hours; Jiang Yutian, Chen Tongming, etc., Synthesis of Flufenacet, "Pesticides", 2007, Volume 46, No. 11, P734-736, reported The method takes more than 9 hours); a large amount of hydrogen peroxide is used in the kettle reaction, and the safety is uncontrollable and other defects

Method used

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  • Method for preparing herbicide flufenacet intermediate tda-sulfone
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  • Method for preparing herbicide flufenacet intermediate tda-sulfone

Examples

Experimental program
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Effect test

Embodiment 1

[0043] 1) The device used: using figure 2 Schematic diagram of the reaction apparatus and equipment used; and image 3 A schematic diagram of the process shown.

[0044] 2) Select toluene as a solvent, dissolve the raw material 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole in an appropriate amount of solvent toluene to form 2-methylthio-5-trifluoromethyl The solution of base-1,3,4-thiadiazole raw material, the raw material concentration is 26%;

[0045] 3) Dissolve the catalyst phenethylphenol polyoxyethylene ether in an appropriate amount of toluene to form a toluene solution of the catalyst phenethylphenol polyoxyethylene ether, and the catalyst concentration is 5%;

[0046] 4) Parameter control: through metering pump 1 (2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole raw material), metering pump 2 (70% hydrogen peroxide), control 70% hydrogen peroxide and raw materials The molar ratio of 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole is about 2.2:1, where metering ...

Embodiment 2

[0053] 1) The device used: using figure 2 Schematic diagram of the reaction apparatus and equipment used; and image 3 A schematic diagram of the process shown. And the Corning microchannel reactor with exactly the same improvement as in Example 1 was used.

[0054] 2) Select toluene as a solvent, dissolve the raw material 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole in an appropriate amount of solvent toluene to form 2-methylthio-5-trifluoromethyl The solution of base-1,3,4-thiadiazole raw material, the raw material concentration is 26%;

[0055] 3) Parameter control: through metering pump 1 (2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole raw material), metering pump 2 (70% hydrogen peroxide), control 70% hydrogen peroxide and raw materials The molar ratio of 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole is about 2.2:1, where metering pump 1 (2-methylthio-5-trifluoromethyl-1 , 3,4-thiadiazole raw material) flow rate is 14.4 mL / min, and the flow rate of metering p...

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Abstract

The invention discloses a continuous flow synthetic method for preparing 2-methylsulfonyl-5-trifluoromethyl-1,3,4-thiadiazole by oxidizing 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole. Compared with the prior art, the reaction time is shortened from the conventional 9-11 hours to few minutes, and the reaction efficiency is significantly improved; and the reaction adopts continuous flow, so that the accumulation of a large amount of peroxides at a high reaction temperature is avoided, and the inherent safety of the process is improved.

Description

technical field [0001] The invention relates to a synthesis method of sulfone compounds, in particular to a continuous flow synthesis method of sulfone compounds, belonging to the technical field of chemical production. Background technique [0002] Flufenacet, English name: N-(4-fluorophenyl)-N-(1-me-thylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy] Acetamide, CAS number: 142459-58-3, molecular formula: C 14 h 13 f 4 N 3 o 2 S, molecular weight: 363.3, relative density: 1.312 (25). Physical and chemical properties: white to brown solid, melting point 75-77°C. Flufenacet is an oxyacetanilide herbicide, developed by Bayer AG in 1988, with test code BAYFOE5043, common name Flufenact, and trade names Axiom, Herald, Terano, Epic, Arist. Flufenacet is another oxyacetanilide herbicide following the successful development of mefenacet by Bayer in Germany. It mainly works by inhibiting cell division. From 1988 to 1994, a large number of field experiments were don...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/125
CPCC07D285/125
Inventor 杨维清胡嘉彭昌荣杨玉强任川宏蒋红
Owner SHANGHAI LINKCHEM TECH CO LTD
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