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A kind of improved synthetic technique of fluopyram

A fluopyram and synthesis process technology, which is applied in the field of improved synthesis process of fluopyram, can solve problems such as unsatisfactory yield and unfavorable industrialization, and achieve product purity improvement, post-treatment simplification, and mild reaction conditions Effect

Active Publication Date: 2021-03-02
DALIAN JOIN KING FINE CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After the improvement, the reaction conditions are mild, and the yield is greatly improved, but there are still some defects. Different solvents are used for the two-step decarboxylation, and the intermediate needs to be separated, and then the solvent is switched for the next step. The yield is not very ideal, which is not conducive to industrialization

Method used

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  • A kind of improved synthetic technique of fluopyram
  • A kind of improved synthetic technique of fluopyram

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Put 2-(3-chloro-5-trifluoromethyl-2-pyridyl)-2-[(2-trifluoromethylbenzoyl)aminomethyl]-1,3- into a 1000mL four-necked bottle Dimethyl malonate 28.5g (0.05mol, 95%, 1.0eq), methanol 150mL, potassium carbonate aqueous solution 125mL (0.25mol, 2M, 5.0eq), heat the system to 60°C and keep it warm for 4h, sample HPLC to detect raw materials The reaction was complete to obtain α-(2-trifluoromethylbenzoyl)aminomethyl-3-chloro-5-trifluoromethyl-2-pyridyl acetate potassium solution;

[0032] Add 200mL of citric acid aqueous solution (0.2mol, 1M, 4.0eq) dropwise to the above system to adjust the pH of the system to 4-5, then keep it warm at 60°C for 4h, and the secondary deacidification reaction controlled by HPLC is complete. The reaction solution was cooled to room temperature 20-25° C., filtered and washed with water to obtain 19.6 g of fluopyram with a content of 99.2% and a yield of 95.0%. The crude product of fluopyram was washed with n-heptane under reflux to obtain a ref...

Embodiment 2

[0034] Put 2-(3-chloro-5-trifluoromethyl-2-pyridyl)-2-[(2-trifluoromethylbenzoyl)aminomethyl]-1,3- into a 1000mL four-necked bottle Dimethyl malonate 28.5g (0.05mol, 95%, 1.0eq), acetonitrile 150mL, sodium hydroxide aqueous solution 100mL (0.4mol, 4M, 8.0eq), the system was heated to 30°C and kept for 3h, and the sample was detected by HPLC The raw materials were reacted completely to obtain α-(2-trifluoromethylbenzoyl)aminomethyl-3-chloro-5-trifluoromethyl-2-pyridyl sodium acetate solution;

[0035]Add 40mL of acetic acid aqueous solution (0.32mol, 8M, 6.4eq) dropwise to the above system to adjust the pH of the system to 4-5, then keep warm at 60°C for 4h, and the secondary deacidification reaction controlled by HPLC is complete. The reaction liquid was cooled to room temperature 20-25° C., filtered and washed with water to obtain 19.1 g of fluopyram with a content of 98.8% and a yield of 93.2%. The crude product of fluopyram was washed with n-heptane under reflux to obtain ...

Embodiment 3

[0037] Put 2-(3-chloro-5-trifluoromethyl-2-pyridyl)-2-[(2-trifluoromethylbenzoyl)aminomethyl]-1,3- into a 1000mL four-necked bottle Dimethyl malonate 28.5g (0.05mol, 95%, 1.0eq), DMF150mL, sodium formate aqueous solution 25mL (0.1mol, 4M, 2.0eq), heat the system to 90°C and keep it for 1h, sample HPLC to detect the complete reaction of raw materials , to obtain α-(2-trifluoromethylbenzoyl)aminomethyl-3-chloro-5-trifluoromethyl-2-pyridyl sodium acetate solution;

[0038] Add 100mL of formic acid aqueous solution (0.2mol, 2M, 1.6eq) dropwise to the above system to adjust the pH of the system to 4-5, then keep it warm at 90°C for 3h, and the secondary deacidification reaction controlled by HPLC is complete. The reaction liquid was cooled to room temperature 20-25° C., filtered and washed with water to obtain 19.8 g of fluopyram with a content of 99.0% and a yield of 96.0%. The crude product of fluopyram was washed with n-heptane under reflux to obtain a refined product with a pu...

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Abstract

The invention discloses an improved synthesis process of fluopyram, which belongs to the technical field of fine chemicals. The process is based on 2-(3-chloro-5-trifluoromethyl-2-pyridyl)-2-[(2-trifluoromethylbenzoyl)aminomethyl]-1,3-malonic acid The diester is used as a raw material, and in the same solvent, undergoes two steps of hydrolysis and decarboxylation in alkaline and acidic steps respectively, and undergoes conventional post-treatment methods to obtain the target product. The technical route selection of the present invention is reasonable and convenient, realizes the process connection of two-step decarboxylation, has mild reaction conditions, simplifies post-treatment, is easy for industrialized production, and has a total separation yield of over 96%.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to an improved synthesis process of fluopyram. Background technique [0002] Fluopyram (fluopyram), its chemical name is N-[2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl]-2-trifluoromethylbenzamide, It is a new type of benzamide fungicide developed by Bayer CropScience, which inhibits mitochondrial respiration by blocking the electron transfer of succinate dehydrogenase in the respiratory chain. [0003] Fluopyram inhibits spore germination, germ tube growth, mycelium growth, and sporulation. In plants, fluopyram can conduct and transfer in the xylem, and is mainly used to prevent gray mold, powdery mildew, late blight, downy mildew, and rice blast caused by fungal pathogens. It has been used in more than 70 kinds of crops, such as grapes, pome fruit, stone fruit, vegetables and field crops, etc. No matter it is used alone or in combination, it shows high activity, and it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 王俊春王荣良徐德胜田颖
Owner DALIAN JOIN KING FINE CHEM CO LTD
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