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Method for catalytically synthesizing pyraclostrobin

A technology for synthesizing pyrazole ether and strobilurin, which is applied in organic chemistry and other fields, can solve problems such as harsh reaction conditions, incomplete reaction, and long reaction time, and achieve short reaction time, control of process water consumption, and high product yield Effect

Inactive Publication Date: 2016-09-21
SHIJIAZHUANG SENTAY CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although this synthesis method can achieve the purpose of synthesizing pyraclostrobin, there are disadvantages in the preparation process: (1) the reaction conditions are harsh, the reaction system requires low moisture, and compound II needs to be dried before reacting; (2) After dropping dimethyl sulfate, the reaction time is long and the reaction is not complete; (3) The sodium carbonate or potassium carbonate used is excessive, and the post-treatment process needs to add a large amount of water to dissolve the formed inorganic salts, resulting in a large amount of high-salt wastewater

Method used

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  • Method for catalytically synthesizing pyraclostrobin
  • Method for catalytically synthesizing pyraclostrobin
  • Method for catalytically synthesizing pyraclostrobin

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Add 373.8 g (1 mol) of compound II to a two-phase solvent consisting of 2250 mL of chloroform and 350 mL of water, add 11.2 g of tetrabutylammonium bromide, raise the temperature to reflux, and dropwise add 173 g of 30% (1.3 mol) of sodium hydroxide aqueous solution and 164g (1.3 mol) of dimethyl sulfate, keeping the pH of the reaction system = 8-9, adding dropwise in 2 hours, stirring at reflux for 2 hours, cooling down to room temperature, separating the aqueous phase, and subtracting the organic phase Concentrate under reduced pressure, add crystallization solvent isopropanol to the concentrate, and filter to obtain compound Ⅰ, 373 g of light yellow crystals, HPLC assay (external standard) content 98.8%, yield 96.2%, mp: 63-65°C.

[0026] 1 H-NMR (400MHz, CDCl 3 ): δ = 3.761(3H, s, -CH 3 ), δ = 3.795(3H, s, -CH 3 ), δ = 5.345(2H, s, -CH 2 ), δ = 5.9215.927(1H, d, -CH), δ = 7.344~7.405(5H, m, Phenyl-H, -CH), δ = 7.5147.551(2H, d, Phenyl-H), δ = 7.6537.693(2H, m, ...

Embodiment 2

[0029] Add 373.8 g (1 mol) of compound II to a biphasic solvent consisting of 1699 mL of dichloromethane and 170 mL of water, add 22.4 g of tetrabutylammonium chloride, raise the temperature to 39-42 ° C, and drop 173 g of 30 % (1.3 mol) sodium hydroxide aqueous solution and 164g (1.3 mol) dimethyl sulfate, keep the pH of the reaction system = 8-9, add dropwise in 2 hours, keep stirring at 39-42°C for 2 hours, cool to room temperature, divide The aqueous phase was removed, and the organic phase was concentrated under reduced pressure. The crystallization solvent isopropanol was added to the concentrate, and compound Ⅰ was obtained by filtration, 370 g of light yellow crystals. The content determined by HPLC (external standard) was 98.3%, and the yield was 95.4%.

Embodiment 3

[0031] Add 373.8 g (1 mol) of compound II to a biphasic solvent composed of 2250 mL 1,2-dichloroethane and 350 mL water, add 11.2 g tetrabutylammonium bromide, and heat up to 60°C-65°C, At the same time, add 173 g of 30% (1.3 mol) sodium hydroxide aqueous solution and 164 g (1.3 mol) of dimethyl sulfate dropwise, keep the pH of the reaction system = 8-9, complete the dropwise addition in 2 hours, keep stirring at 60°C-65°C for 2 hours, lowered to room temperature, separated the water phase, concentrated the organic phase under reduced pressure, added crystallization solvent isopropanol to the concentrate, and filtered to obtain compound Ⅰ, 370 g of light yellow crystals, the content of which was determined by HPLC (external standard) was 98.5%, and the yield was The rate is 95.4%.

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Abstract

The invention discloses a method for catalytically synthesizing pyraclostrobin, relating to the technical fields of chemical industry and pesticide intermediate preparation. The method comprises the following steps: adding a compound II N-hydroxy-N-2-[(N-p-chlorphenyl)-3-pyrazolyloxymethyl]carbanilate into a two-phase solvent, adding a phase-transfer catalyst, and meanwhile, dropwisely adding an acid-binding agent water solution and dimethyl sulfate to carry out etherification reaction on the compound II N-hydroxy-N-2-[(N-p-chlorphenyl)-3-pyrazolyloxymethyl]carbanilate and dimethyl sulfate while keeping the pH value of the reaction system at 8-9, thereby obtaining the compound I pyraclostrobin. The method has the advantages of short reaction time and high product yield, lowers the production cost, and reduces the generated wastewater, thereby being beneficial to environment protection.

Description

technical field [0001] The invention relates to the technical field of pyraclostrobin preparation. Background technique [0002] Pyraclostrobin (chemical name: N-methoxy-N-[(N-p-chlorophenyl)-3-pyrazolyloxymethyl]phenylcarbamate, compound Ⅰ), is a German BASF In 1993, the company discovered a new type of broad-spectrum Strobin fungicide containing a pyrazole structure. It is mainly used for stem and leaf spraying, which can effectively prevent and control crop diseases caused by Ascomycetes, Basidiomycetes, Oomycetes and Deuteromycetes. It also has the characteristics of low ecological risk and high efficacy selectivity. It is widely used to prevent and control diseases of wheat, peanut, rice, vegetable and fruit trees and field crops. Has been listed as a "Candidate Reduced Risk Agent" by the US Environmental Protection Agency. [0003] The synthetic route of pyraclostrobin etherification is mainly N-hydroxy-N-2-[(N-p-chlorophenyl)-3-pyrazolyloxymethyl]phenylcarbamate (c...

Claims

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Application Information

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IPC IPC(8): C07D231/22
CPCC07D231/22
Inventor 刘倩吴国军赵彦华
Owner SHIJIAZHUANG SENTAY CHEM CO LTD
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