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Novel compound, and method for preparing topramezone intermediate from novel compound

A compound, dihydroisoxazole technology, applied in the field of synthesis of key intermediates, can solve the problems of unavoidable side reactions, poor selectivity of bromination reaction, avoid by-products, safe and controllable production, mild and acceptable reaction conditions. control effect

Active Publication Date: 2021-05-04
HEBEI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0020]4. In route one, the selectivity of bromination reaction is poor, and side reactions are inevitable

Method used

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  • Novel compound, and method for preparing topramezone intermediate from novel compound
  • Novel compound, and method for preparing topramezone intermediate from novel compound
  • Novel compound, and method for preparing topramezone intermediate from novel compound

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preparation example Construction

[0129] Regarding the synthetic reaction conditions in the preparation method provided by the present invention, those skilled in the art can understand that any condition that can realize the conversion from reactants to products should be within the protection scope of the present invention. The inventor's contribution First of all, it is reflected in the design of the route to obtain the product through a suitable intermediate, and it is also reflected in the optimization of the reaction conditions to achieve the above transformation. Considering that the synthesis technology is constantly improving, new synthesis technologies may emerge in the future, such as microbial transformation, the use of new catalysts, etc., as long as the above-mentioned conversion from reactants to products is realized, it should be within the protection scope of the present invention.

[0130] In a specific embodiment, the present invention also provides a preparation method for synthesizing the f...

Embodiment 1-1

[0177] The preparation of embodiment 1-1 compound II (2-methyl-3-chloromethyl-6-methylthiobenzonitrile)

[0178] Dissolve 16.3 g of compound I (2-methyl-6-methylthiobenzonitrile) in a mixed solution of 100 mL of hydrofluoric acid and 50 mL of 85% phosphoric acid, stir and add 30.0 g of paraformaldehyde, and continuously and slowly pass in hydrogen chloride gas , stirred at 50° C. for 4 hours, monitored by thin-layer chromatography, compound 1 was almost completely consumed, and the flow of hydrogen chloride gas was stopped. Cool to room temperature, add 200mL distilled water, extract with ethyl acetate (50mL×3), collect the organic phase and successively wash with 50mL saturated aqueous sodium bicarbonate solution and 50mL saturated brine, dry over anhydrous sodium sulfate, filter, and evaporate the solvent under reduced pressure , 18.0 g of the target product (2-methyl-3-chloromethyl-6-methylthiobenzonitrile) was obtained by column chromatography, yield: 85.2%.

[0179] ESI-...

Embodiment 1-2

[0180] The preparation of embodiment 1-2 compound II (2-methyl-3-chloromethyl-6-methylthiobenzonitrile)

[0181] Dissolve 16.3g of compound I (2-methyl-6-methylthiobenzonitrile) in 100mL of dichloromethane solvent, stir and add 13.3g of aluminum trichloride, then add 30.0g of methylal, and continue to slowly pass through Add hydrogen chloride gas and stir at 30°C for 6 hours. Monitored by thin layer chromatography, the raw material compound I is almost completely consumed, and the gas flow is stopped. Cool to room temperature, add 200mL distilled water, extract with dichloromethane (50mL×3), collect the organic phase and successively wash with 50mL saturated aqueous sodium bicarbonate solution and 50mL saturated brine, dry over anhydrous sodium sulfate, filter, and evaporate the solvent under reduced pressure 16.5 g of the target product (2-methyl-3-chloromethyl-6-methylthiobenzonitrile) was obtained by column chromatography, yield: 77.8%, which was confirmed as the compound b...

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Abstract

The invention provides a compound as shown in a general formula A. In the compound, R1 is a halogenated alkyl group, a hydroxyalkyl group, an aldehyde group or a carboxylic acid group; R2 is a methyl groupa; R3 is a cyano group, a chlorine substituted oximido group, or a 4, 5-dihydroisoxazole-3-yl group; and R4 is an alkyl substituted sulfenyl group, an alkyl sulfonyl group or an alkyl sulfoxide group, and the alkyl group is independently selected from methyl, ethyl, propyl and isopropyl. The invention also provides the compound as one or more intermediates for preparing topramezone. In addition, the invention provides a method for preparing a topramezone compound. The topramezone compound is prepared by taking the compound as shown in the general formula A as an intermediate, and the key intermediate of topramezone is finally prepared through chloromethylation or hydroformylation, hydrolysis, hydroxyamination reaction, diazotization halogenation, dipolar cycloaddition and oxidation reaction. The reaction conditions provided by the invention are mild and controllable, the reaction selectivity of each step is good, the yield is relatively high, the generation of some byproducts is avoided, and the product quality is ensured. The whole process route is easy to realize industrialization.

Description

technical field [0001] The present invention relates to a series of novel compounds and their preparation methods for herbicides. Specifically, the present invention provides a method for synthesizing a key intermediate of fenflumezone. Background technique [0002] Currently, 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors are new herbicide targets identified in the 1990s by inhibiting 4-hydroxyphenylpyruvate dioxygenase in plastoquinone biosynthesis Oxidase (4-HPPD), which indirectly affects the synthesis of carotenoids, interferes with the synthesis and function of chloroplasts under light, and eventually leads to the death of weeds. The mechanism of action of 4-HPPD inhibitors in animals and plants is different, and it is safe for mammals. So far, the HPPD inhibitor herbicides that have been developed are still one of the herbicide species with the least toxicity to mammals. Therefore, this is a class of herbicides with good development prospects. [0003] To...

Claims

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Application Information

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IPC IPC(8): C07D261/04C07C319/20C07C323/62C07C323/47
CPCC07D261/04C07C319/20C07C323/62C07C323/47
Inventor 李林何瑞红李媛媛张欣悦汪改欣田梦张云刘兰
Owner HEBEI MEDICAL UNIVERSITY
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