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Synthetic method of 2-methylsulfuryl-5-trifluoromethyl-1,3,4-thiadiazole

The technology of a trifluoromethyl group and a synthesis method, which is applied in the field of organic synthesis reaction, can solve the problems of unfavorable large-scale industrial production of flufenoxamine, high process risk, potential safety hazard, etc., and achieves low cost, improved reaction efficiency, and pollution. less sexual effect

Active Publication Date: 2017-03-08
山东京博农化科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] (2) The process is more dangerous, and the residual hydrogen peroxide carries water through the azeotrope, which has certain potential safety hazards;
[0009] (3) The operation is relatively complicated
[0010] Due to the existence of the above-mentioned shortcomings, it is unfavorable for the large-scale industrial production of flufenacet

Method used

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  • Synthetic method of 2-methylsulfuryl-5-trifluoromethyl-1,3,4-thiadiazole
  • Synthetic method of 2-methylsulfuryl-5-trifluoromethyl-1,3,4-thiadiazole

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Add 50.1g (0.25mol, content 99%) of 2-methylthio-5-trifluoromethyl-1,3,4- Thiadiazole, 3.1g acetic acid, 0.02g sodium tungstate, 0.15g tetrabutylammonium chloride, stir and heat up to 53°C, start to add 90.7g (0.8mol, content 30%) hydrogen peroxide dropwise, after the dropwise addition, 54°C Insulate for 5 hours, cool down to 0°C, filter with suction, and dry to obtain snow-white scaly crystals: 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole, purity 98.9 %, yield 96.3%.

Embodiment 2

[0031] Add 100.2g (0.5mol, content 99%) of 2-methylthio-5-trifluoromethyl-1,3,4- Thiadiazole, 10g acetic acid, 0.05g sodium tungstate, 0.11g tetrabutylammonium chloride, stir and heat up to 52°C, start to add 168g (1.5mol, content 30%) hydrogen peroxide dropwise, after the dropwise addition, keep at 55°C for 5h , cooled to -2°C, suction filtered, and dried to obtain snow-white scaly crystals: 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole, purity 99.1% , yield 96.3%.

Embodiment 3

[0033] Add 200.4g (1mol, content 99%) of 2-methylthio-5-trifluoromethyl-1,3,4-thiadiol to a 1000ml four-necked bottle equipped with mechanical stirring, a constant pressure dropping funnel, and a thermometer Oxadiazole, 15g acetic acid, 0.1g sodium tungstate, 0.4g benzyltriethylammonium bromide, stir and heat up to 55°C, start to add 336g (3mol, content 30%) hydrogen peroxide dropwise, after the dropwise addition, keep at 55°C for 6h , cooled to 1°C, suction filtered, and dried to obtain snow-white scaly crystals: 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole with a purity of 99.0%. Yield 96.4%.

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Abstract

The invention belongs to the field of organic synthesis, belongs to pesticide synthesis technologies, and in particular relates to a synthetic method of 2-(methylsulfuryl)-5-(trifluoromethyl)-1,3,4-thiadiazole. According to the synthetic method, 2-( methylthio)-5-(trifluoromethyl)-1,3,4-thiadiazole is used as a raw material, and a phase transfer catalyst and sodium tungstate are selected as catalysts for reaction to prepare a target product. According to the method, a reaction environment is optimized, and the reaction efficiency is greatly improved on the premise of not adding an organic solvent, so that the purity and the yield of the product are improved, the reaction temperature is lowered, the risk of oxydol high-temperature backflow zone water is reduced, and then the safety of the reaction is improved.

Description

technical field [0001] The invention belongs to the field of organic synthesis reactions, and relates to the synthesis technology of pesticide intermediates, in particular to the synthesis of the herbicide flufenacet intermediate 2-thiamphenyl-5-trifluoromethyl-1,3,4-thiadiazole method. Background technique [0002] Flufenacet, chemical name: 4'-fluoro-N-isopropyl-2-[5-(trifluoroglycoside)-1,3,4-thiadiazo-2-imine]acetamide. Physical properties: The pure product is white crystal. 2-thiamphenicol-5-trifluoromethyl-1,3,4-thiadiazole is an intermediate in the synthesis of flufenacet, and it is the step with the lowest yield. Increasing the yield and quality is beneficial to the enhancement. As an aryloxyamide herbicide, flufenacet mainly acts by inhibiting cell division and growth, and can effectively control many annual grass weeds. In addition, the herbicide has low toxicity to animals and is easily degraded in the environment . [0003] Patent CN1126748C reports that bori...

Claims

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Application Information

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IPC IPC(8): C07D285/125
CPCC07D285/125
Inventor 王帅帅戴荣华曹学兵张华王宗逄廷超
Owner 山东京博农化科技股份有限公司
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