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Synthesis method of fluopyram

A technology of fluopyram and fluopyram, which is applied in the field of fluopyram synthesis, can solve the problems of many side reactions in the synthesis of intermediate products, high decarboxylation temperature, and long reaction time, and achieve good industrial value and convenience The effect of recycling and short process route

Inactive Publication Date: 2019-11-12
DALIAN JOIN KING FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The synthesis route of this method is longer, and there are many side reactions in the synthesis of intermediate products, and it is not easy to purify. In addition, the decarboxylation temperature in the last step is very high, the reaction time is very long, and the coking is serious, resulting in a very low yield of the whole route, which is not conducive to realizing industrial production.

Method used

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  • Synthesis method of fluopyram
  • Synthesis method of fluopyram
  • Synthesis method of fluopyram

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Put DCTF54.3g (0.25mol, 99.5%, 1.0eq), NMP200mL, potassium hydroxide solid 24.8g (0.375mol, 85%, 1.5eq) into a 500mL four-necked flask, and heat up to 70-80°C. Add 34.3g of ethyl cyanoacetate (0.3mol, 99% industrial product, 1.2eq) dropwise to the system, there is exothermic phenomenon, the temperature is controlled at 70-80°C, the dropwise addition is completed in about 0.5h, and the reaction is kept at 70-80°C 2h, HPLC monitors that the reaction of raw materials is complete.

[0030] Add 76.0g of concentrated hydrochloric acid (0.75mol, 36%, 3.0eq) dropwise to the system, there is a slight temperature rise phenomenon, the system emits a large amount of white smoke, a yellow solid is generated, and tail gas is released, and the system is continued to heat up to reflux reaction for 5h, HPLC detects that the reaction of the intermediate is complete, and the system is a brown-yellow suspension.

[0031] After the system was cooled down, the solvent was desolvated under r...

Embodiment 2

[0033] Into a 500mL autoclave, 34.3g (0.15mol, 96.6%, 1.0eq) of 2-acetonitrile-3-chloro-5-trifluoromethylpyridine and 50.9g (0.18mol, 97%, 1.2eq) of mixed acid anhydride were added, 5% Pd / C dry basis 1.7g, toluene 100mL, close the autoclave, nitrogen replacement three times. Pass hydrogen to the system to 1.5MPa, heat up to 20-30°C and keep it warm for reaction, keep the pressure at 1.5-2.0Mpa for 10h, and stop the ventilation if the pressure does not drop.

[0034] After pressure relief and exhaust, sample HPLC to monitor the conversion of raw materials, filter the reaction solution, rinse with an appropriate amount of toluene, and combine the mother liquor and washing solution. Add dropwise 5% sodium carbonate aqueous solution to the mother liquor to neutralize to pH = 8-9, separate layers, and desolventize the organic layer under reduced pressure to obtain 55.9 g of the crude product of fluopyram, the target product, with a content of 87.8% and a yield of 82.5%. The crude ...

Embodiment 3

[0037] Into a 500mL autoclave, 34.3g (0.15mol, 96.6%, 1.0eq) of 2-acetonitrile-3-chloro-5-trifluoromethylpyridine and 44.5g (0.158mol, 97%, 1.05eq) of mixed acid anhydride were added, Raney nickel 3.4g, chlorobenzene 100mL, close the autoclave, nitrogen replacement three times. Pass hydrogen to the system to 1.5MPa, heat up to 50-60°C and keep it warm for reaction, keep the pressure at 1.5-2.0Mpa for 12 hours, stop the ventilation if the pressure does not drop.

[0038] After pressure relief and exhaust, sample HPLC to monitor the conversion of raw materials, filter the reaction solution, rinse with an appropriate amount of toluene, and combine the mother liquor and washing solution. 5% sodium hydroxide aqueous solution was added dropwise to the mother liquor to neutralize to pH = 8-9, the layers were separated, and the organic layer was precipitated under reduced pressure to obtain 54.8 g of the target product fluopyram with a content of 92.6% and a yield of 85.3%.

[0039]T...

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Abstract

The invention discloses a synthesis method of fluopyram and belongs to the technical field of fine chemical engineering. The synthesis method comprises the following steps: by taking 2,3-dichloro-5-trifluoromethylpyridine as a raw material, performing condensation and hydrolysis decarboxylation with ethyl cyanoacetate in the presence of an alkali so as to obtain 2-acetonitrile-3-chloro-5-trifluoromethylpyridine; performing catalytic hydrogenation reduction so as to obtain 2-ethylamino-3-chloro-5-trifluoromethylpyridine, performing protection by using o-trifluoromethyl benzoic anhydride or o-trifluoromethyl benzoic acid-trimethylacetic anhydride, so as to obtain a target product, namely fluopyram. The synthesis method is reasonable and simple and convenient in route selection and is applicable to industrial amplification, the synthesis method breaks through a conventional process, a step that hydrogenation reduction is implemented and at the same time amino is protected by using other acylation reagents firstly, and acylation of the amino with o-trifluoromethyl benzoyl chloride is implemented later is avoided, a step that hydrogenation is implemented and at the same time protectionis implemented to obtain the target product amide is implemented instead, and process procedures can be simplified.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a method for synthesizing 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. Fluopyram inhibits spore germination, germ tube growth, mycelium growth, and sporulation. In plants, fluopyram can be conducted and transferred in the xylem. It is mainly used to control gray mold, powdery mildew, late blight, downy mildew, and rice blast caused by fungal pathogens. It can be used for more than 70 kinds of crops, including grapes, pome fruit, stone fruit, vegetables and field crops. Regardless of single use or mixed use, they all show high activity, and their applicati...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 王俊春王荣良吕超
Owner DALIAN JOIN KING FINE CHEM CO LTD
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