Method for synthesizing fluensulfone

A technology of fluthiandin and thiazole, which is applied in the field of synthesis and preparation of pesticide raw materials, can solve the problems of environmental pollution, many solid wastes and the like, and achieves the effects of high yield, short reaction steps and low cost

Inactive Publication Date: 2020-06-05
HEBEI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Later, some people switched to potassium hydrogen persulfate oxidation (US20060004196), but there are many solid wastes and environmental pollution problems, so further improvement is still needed

Method used

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  • Method for synthesizing fluensulfone
  • Method for synthesizing fluensulfone
  • Method for synthesizing fluensulfone

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Example 1 Synthesis of 2-(3,3,4-trifluoro-3-butenylmercapto)thiazole

[0026] Under nitrogen protection, 26g mercaptothiazole, 33.6g sodium carbonate were used as catalyst and acid binding agent and 46g 4-chloro-1,1,2-trifluoro-1-butene were reacted, heated in 300ml dimethylformamide After reflux for 6-8 hours, after cooling to room temperature, filter the mixture, evaporate the solvent, dissolve the residue with 200ml of dichloromethane, wash with 200ml of 5% aqueous sodium hydroxide solution and 200ml of water successively, and then dry with anhydrous sodium sulfate. Filter and spin dry to obtain 40 g of 2-(3,3,4-trifluoro-3-butenylmercapto)thiazole with a yield of 80%.

Embodiment 2

[0027] Example 2 Synthesis of 2-(3,3,4-trifluoro-3-butenylmercapto)-5-chlorothiazole

[0028] 40g of 2-(3,3,4-trifluoro-3-butenylmercapto)thiazole was dissolved in 350ml of dichloromethane, 28.5g of dichlorohydantoin was added to the solution, and heated to reflux for 18 hours under nitrogen protection . After cooling to room temperature, the solid was filtered out, the reaction solution was washed with water, and the solvent was distilled off to obtain 45 g of 2-(3,3,4-trifluoro-3-butenylmercapto)-5-chlorothiazole. The yield is 98%.

Embodiment 3

[0029] Example 3 Synthesis of fluthiazol

[0030] Add 45g of 2-(3,3,4-trifluoro-3-butenylmercapto)-5-chlorothiazole to 45ml of water, add 1.74g of catalyst sodium phosphotungstate, and then within 30min at 5°C, While stirring, 67 g of hydrogen peroxide was added dropwise. The temperature was raised to 65°C and stirred for 1 hour. The peroxide test was performed by adding 18 g of sodium bisulfite to remove excess hydrogen peroxide. Filter and spin off the methanol component. Extracted with 50ml of ethyl acetate, dried over sodium sulfate, and spin-dried to obtain 43g of yellow oil with a yield of 86%. 1 HNMR (500 MHz, CDCl 3 ), δ: 7.89 (s, 1H), 3.64 (m, 2H), 2.93 (d, J = 19.6, 7.0, 3.2 Hz, 2H). 13 CNMR (125MHz, CDCl 3 ), δ: 19.90, 20.10, 29.33, 50.38, 135.41, 143.35, 162.51.

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Abstract

The invention discloses a method for synthesizing fluensulfone. The method particularly includes: 2-mercaptothiazole and 4-bromo-1,1,2-trifluoro-1-butene react to synthesize 2-(3,3,4-trifluoro-3-butenylsulfydryl)thiazole, then N-chlorosuccinimide is used for chlorination to synthesize 2-(3,3,4-trifluoro-3-butenylsulfydryl)-5-chlorothiazole, and finally hydrogen peroxide is adopted as an oxidizingagent to oxidize thioether in one step. The method has the characteristics of simple synthesis method, high product purity, environment friendliness and low preparation cost.

Description

technical field [0001] The invention relates to a method for synthesizing fluthiazol, and belongs to the technical field of synthesis and preparation of pesticide raw materials. Background technique [0002] In recent years, with the increasingly serious environmental pollution, the requirements for environmental protection have become higher and higher. In terms of the use of pesticides, the total amount required by our country has only decreased but not increased. Therefore, the research and development direction of pesticides has shown high efficiency, low toxicity, and low residue. features. Since 2015, the newly registered or marketed pesticides around the world basically revolve around this direction. Fluensulfone (Fluensulfone, trade name: MCW-2; test code: BYI1921, MAI-08015, MAI-08016; other names: Nimitz, biflusulfone, flusulfone) is a fluorine developed by Makhteshim Chemical Works. Olefin-based nematicides. The structure is as follows: [0003] [0004] Fl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/36
CPCC07D277/36
Inventor 刘庆彬冯官生王宝张福军
Owner HEBEI NORMAL UNIV
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