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Fluopyram synthesis method

A technology of fluopyram and a synthesis method, which is applied in the field of chemical synthesis, can solve the problems of prolonged process flow, low yield, complicated hydrogenation reaction, etc., and achieves cheap and easy availability of raw materials, improved reaction yield, and enhanced mass transfer. effect of the process

Pending Publication Date: 2022-07-29
利民化学有限责任公司
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] The first type: represented by the Chinese patent applications whose application numbers are CN101080390B and CN111056997A, is obtained by condensing 2,3-dichloro-5-(trifluoromethyl)-pyridine as a raw material with ethyl cyanoacetate and hydrolyzing decarboxylation 2-Acetonitrile-3-chloro-5-trifluoromethylpyridine, then protected by catalytic hydrogenation and acetic anhydride to obtain 2-acetamidoethyl-3-chloro-5-trifluoromethylpyridine, and then through acidic Hydrolysis to obtain 2-ethylamino-3-chloro-5-trifluoromethylpyridine hydrochloride, and finally amidation with o-trifluoromethylbenzoyl chloride to obtain the target product fluopyram, the existing problems are: The steps are complicated, and the process involves a high-temperature hydrogenation process, which has high risk, high cost, and low yield, making it difficult to industrialize production
Its disadvantages are: the one-pot hydrogenation reaction involved in the process is complicated, the target yield is low, and hydrogenation equipment is still required, making it difficult to form industrialization
[0006] Others: as the process shown in the Chinese patent application with the application number CN108822024A, the reaction steps are many, and the total yield of fluopyram is only 63%; as the process shown in the Chinese patent application with the application number CN110437138A, the initial The materials are expensive, and industrial raw materials cannot be purchased, so they can only be synthesized by themselves; the process flow is prolonged in disguise; as shown in the Chinese patent application with the application number CN112979539A, the intermediate 3-chloro-5-trifluoromethyl-2 needs to be prepared -pyridylethyl (diethyl ester)-2-trifluoromethylbenzamide, the route is longer to prepare fluopyram, and the actual yield is lower; as shown in the Chinese patent application with application number CN113429338A, It requires the use of alkyllithium, which is prone to spontaneous combustion with oxygen and water in the air, and it is difficult to realize industrialization

Method used

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  • Fluopyram synthesis method

Examples

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Effect test

Embodiment 1

[0039] A method for synthesizing fluopyram, comprising the following steps:

[0040] Step A: According to the molar mass and volume ratio of 2-trifluoromethylbenzoic acid, thionyl chloride and reaction solvent A, 1mol:1mol:1L, add 190.12g of 2-trifluoromethylbenzoic acid to a 2L there-necked flask, and react Solvent A 1 L of 1,2 dichloroethane, stir and mix at 15 ° C, then slowly add 118.97 g of thionyl chloride, heat up to 60 ° C, keep the reaction for 3 hours, control the reaction solution, detect the raw material ≤ 0.2%, and then at - 0.098mP was desolvated under reduced pressure to 85°C, and the reaction solvent A and the remaining thionyl chloride were removed to obtain 206.45g of intermediate I 2-trifluoromethylbenzoyl chloride, with a content of 99% and a single-step yield of 98%;

[0041] Step B: Under nitrogen protection, after mixing 71.08 g of N-vinylformamide with 500 ml of dry THF, slowly add 120 g of acid binding agent triethylamine, then cool the reaction soluti...

Embodiment 2

[0044] A synthetic method of fluopyram, comprising the following steps:

[0045] Step A: same as Example 1, to obtain Intermediate I 2-trifluoromethylbenzoyl chloride 205.9g, the content is 99%, and the single-step yield is 98%;

[0046] Step B: same as Example 1, obtain 210.87 g of intermediate IIN-vinyl-2-(trifluoromethyl)benzamide, content 94%, single-step yield 94%;

[0047] Step C: Intermediate II N-vinyl-2-(trifluoromethyl)benzamide 210.87g, 2-bromo-3-chloro-5-(trifluoromethyl)pyridine 280g, sodium formate 68.01g, catalyst A 0.5 g of 10-phenylphenothiazine and 0.1 g of catalyst B cyclohexanethiol were added to 1 L of reaction solvent C dimethyl sulfoxide (purity 95%) at the same time. After stirring and dissolving, at room temperature, pumped continuously In the borosilicate glass microreactor, turn on the blue light, set the wavelength band to 420, adjust the pressure in the reactor to 2MP, set the reaction flow time to 45s, and in the borosilicate glass microreactor, ...

Embodiment 3

[0049] A method for synthesizing fluopyram, comprising the following steps:

[0050] Step A: Same as Example 1; 206.3 g of intermediate I 2-trifluoromethylbenzoyl chloride was obtained, with a content of 99% and a single-step yield of 98%;

[0051] Step B: same as Example 1; Intermediate IIN-vinyl-2-(trifluoromethyl)benzamide 211.77g, content 93.6%, single-step yield 94%;

[0052] Step C: Intermediate II N-vinyl-2-(trifluoromethyl)benzamide 211.77g, 2-bromo-3-chloro-5-(trifluoromethyl)pyridine 280g, sodium formate 68.01g, catalyst A 0.5 g of 10-phenylphenothiazine and 0.1 g of catalyst B cyclohexanethiol were added to 1 L of reaction solvent C dimethyl sulfoxide (purity 95%) at the same time. After stirring and dissolving, at room temperature, pumped continuously In the borosilicate glass microreactor, turn on the blue light, set the wavelength band to 420, adjust the pressure in the reactor to 1MP, set the reaction flow time to 30s, and pass the pyridyl halide radical in the...

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Abstract

The invention relates to a fluopyram synthesis method, which comprises: A, carrying out an acylating chlorination reaction on 2-trifluoromethyl benzoic acid and thionyl chloride to obtain an intermediate I 2-trifluoromethyl benzoyl chloride; step B, carrying out nucleophilic substitution reaction on the intermediate I 2-(trifluoromethyl) benzoyl chloride and N-vinylformamide, so as to obtain an intermediate II N-vinyl-2-(trifluoromethyl) benzamide; and step C, the intermediate II N-vinyl-2-(trifluoromethyl) benzamide, 2-bromine-3-chloro-5-(trifluoromethyl) pyridine and sodium formate are subjected to a chemical selective intermolecular coupling reaction through pyridyl halide free radical reduction under the photocatalytic condition, selective arylethylamine is obtained, and the target product fluopyram is obtained. The method is green, environment-friendly and high in yield, and can be used for continuous industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing fluopyram. Background technique [0002] Fluopyram is a new broad-spectrum fungicide of the succinate dehydrogenase inhibitor (SDHI) class. It inhibits mitochondrial respiration by acting on the mitochondrial electron transport system complex II (succinate dehydrogenase) of pathogenic bacteria. function, and then achieve the function of preventing and controlling diseases. Because of its unique mechanism of action, this type of fungicide is the fourth milestone in the history of fungicides, and it has no cross-resistance with other fungicides and no cross-resistance with similar products. ,with broadly application foreground. [0003] At present, the synthetic routes of fluopyram mainly include the following; [0004] The first kind: represented by the Chinese patent applications whose application numbers are CN101080390B and CN111056997A, which are o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61
CPCC07D213/61Y02P20/584
Inventor 李新生孙敬权许辉李林虎马衍峰孙丽梅吴新缘徐宁马建军卓成市
Owner 利民化学有限责任公司
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