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Mesotrione impurity, salt thereof, tautomer of mesotrione impurity or tautomer salt of mesotrione impurity and preparation method

A tautomer, mesotrione technology, applied to its tautomer or its tautomer salt and preparation, its salt, mesotrione impurity field, can solve the problem of high impurity content , The effective content of the product is reduced, and the soil function is affected, and the reaction conditions are mild, the drug safety is improved, and the toxic and side effects are reduced.

Active Publication Date: 2021-01-15
HEBEI LINGANG CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] During the production and use of mesotrione, some impurities will be produced. The existence of these impurities will change the appearance and properties of mesotrione, and affect the stability of mesotrione, and the high content of impurities will also cause The effective content of the product is reduced, affecting the use effect, and increasing the toxic and side effects of mesotrione, which may even have negative effects on crops, interfere with the structure of soil biological communities, and affect soil functions

Method used

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  • Mesotrione impurity, salt thereof, tautomer of mesotrione impurity or tautomer salt of mesotrione impurity and preparation method
  • Mesotrione impurity, salt thereof, tautomer of mesotrione impurity or tautomer salt of mesotrione impurity and preparation method
  • Mesotrione impurity, salt thereof, tautomer of mesotrione impurity or tautomer salt of mesotrione impurity and preparation method

Examples

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Embodiment 1

[0059]A preparation method of mesotrione impurity compound 1, its salt, its tautomer or its tautomer salt:

[0060]At 20°C, add 40 g of mesotrione and 800 g of water to a 1000 mL reaction flask, start stirring, add 30 wt% hydrochloric acid solution to adjust the pH to 1.1, add 40 g of iron powder, and sample the liquid phase during the reaction. When the HPLC content of mesotrione is less than 1%, the temperature is increased to 50°C, the cyclization reaction is carried out, and the reaction is carried out for 4 hours, and the filter cake is filtered while it is hot. The filter cake is washed with 240 g of isopropanol. In the mouth flask, add 500g of water to dissolve, then add potassium hydroxide solution with a mass concentration of 30wt%, adjust the pH to 13.8, stir and raise the temperature to 90℃, keep the reaction for 0.5h, filter while hot, add 30wt% to the filtrate % Hydrochloric acid aqueous solution, adjust the pH to 1.2, cool to 30°C for 2h, and filter to obtain the crude pr...

Embodiment 2

[0065]A preparation method of mesotrione impurity compound 1, its salt, its tautomer or its tautomer salt:

[0066]Under the condition of 30℃, add 40 g of mesotrione and 400 g of diethoxymethane to a 1000 mL reaction flask, turn on the stirring, add a sulfuric acid solution with a mass concentration of 30 wt% to adjust the pH to 4.8, add 120 g of zinc powder, and sample the liquid during the reaction In phase control, when the HPLC content of mesotrione is less than 1%, the temperature is raised to 70°C, and the cyclization reaction is carried out for 2 hours. The filter cake is filtered while it is hot. The filter cake is washed with 90 g of ethanol. Add to a four-necked flask, add 100g of water to dissolve, then add 30wt% sodium hydroxide solution, adjust the pH to 14.1, stir and warm to 50℃, keep the reaction for 1h, filter while hot, add the mass concentration to the filtrate Adjust the pH to 2.8 with a 30wt% hydrochloric acid aqueous solution, cool to 0°C and crystallize for 0.5h,...

Embodiment 3

[0070]A preparation method of mesotrione impurity compound 1, its salt, its tautomer or its tautomer salt:

[0071]At 25℃, add 40g mesotrione and 200g methyl tert-butyl ether to a 1000mL reaction flask, start stirring, add 30wt% hydrochloric acid solution to adjust the pH to 2.5, add 60g iron powder, and take samples during the reaction In the liquid phase control, when the HPLC content of mesotrione is less than 1%, the temperature is increased to 60°C, and the cyclization reaction is carried out for 3 hours. The filter cake is filtered while it is hot. The obtained filter cake is washed with 80g methanol, and filtered after washing. Add the cake to a four-neck flask, add 350g of water to dissolve it, then add a 35wt% sodium methoxide solution, adjust the pH to 13.8, stir and raise the temperature to 70°C, keep it warm for 0.5h, filter while hot, and add the mass concentration to the filtrate It is a 30wt% hydrochloric acid aqueous solution, adjusted the pH to 1.8, cooled to 5°C and c...

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Abstract

The invention relates to the technical field of chemical synthesis, and particularly discloses a mesotrione impurity compound 1, a salt thereof, a tautomer of the mesotrione impurity compound 1 or a salt of the tautomer of the mesotrione impurity compound 1, and a preparation method of the mesotrione impurity compound 1. The mesotrione impurity has a structural formula shown as a formula 1. The preparation method of the mesotrione impurity comprises the following steps of: in a solvent, carrying out reduction reaction on mesotrione and reducing metal powder under an acidic condition until theHPLC content of mesotrione is less than 1%, heating to 50-70 DEG C, and carrying out cyclization reaction to obtain the compound shown in the formula 1, the salt thereof, the tautomer of the compoundor thesalt of the tautomer of the compound. The invention provides a brand-new mesotrione impurity compound, provides a reference substance for impurity analysis and research of mesotrione and preparations thereof, and the reference substance can be used for reference positioning, qualitative or quantitative use of impurities in mesotrione raw materials and preparations thereof, and is beneficialto improvement of the medication safety of mesotrione and reduction of toxic and side effects.

Description

Technical field[0001]The present invention relates to the technical field of chemical synthesis, in particular to a salt of mesotrione impurity, its salt, its tautomer or its tautomer and a preparation method thereof.Background technique[0002]Mesotrione is a pre-emergence and post-emergence broad-spectrum selective herbicide capable of inhibiting hydroxyphenylpyruvate dioxidase (HPPD). It can effectively control the main broadleaf grasses and some grass weeds. Mesotrione is easily conducted in the xylem and phloem of plants, and has contact and specific effects. Field efficacy test results have proved that 100 g / L Mesotrione suspension has effects on annual broad-leaved weeds and some gramineous weeds in corn fields, such as abutilon, amaranth, quinoa, polygonum, barnyardgrass, crabgrass, etc. Good control effect, but poor control effect on amaranth and some gramineous weeds. The structural formula of mesotrione is as follows.[0003][0004]Mesotrione will produce some impurities durin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/06
CPCC07D219/06
Inventor 范李科李静吴会帆顾文涛李娟张辰亮郭翠红郭日凯李成果
Owner HEBEI LINGANG CHEM
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