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Fluopyram preparation method

A technology of fluopyram and trifluoromethylpyridine, which is applied in the field of preparation of fluopyram, can solve the problems of excessive three wastes and low reduction reaction yield, and achieve the effect of short steps and avoiding deprotection steps

Active Publication Date: 2019-02-01
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The route synthesizes the final product through 5 steps (including the synthesis of 1-step o-trifluorobenzoyl chloride). In this process, the reduction reaction yield is low, and the three wastes are more

Method used

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Embodiment 1

[0037] The preparation method of fluopyram of the present embodiment has the following steps:

[0038] 2,3-Dichloro-5-trifluoromethylpyridine (10.0 g, 46.5 mmol), potassium carbonate (7.7 g, 55.8 mmol) were added to N,N-dimethylformamide (50 mL). Ethyl cyanoacetate (6.3 g, 55.8 mmol) was added dropwise to the above mixture at room temperature. After the dropwise addition was complete, the reaction was reacted at 70° C. for 3 hours. After the reaction was completed, it was cooled to room temperature. The pH was adjusted to 2-3 with hydrochloric acid, and the reaction solution was stirred at 140°C for 16 hours. The reaction solution was cooled to room temperature, adjusted to pH 8-9 with 30% potassium hydroxide solution, and extracted with ethyl acetate. The organic phase was concentrated and then distilled under reduced pressure to obtain 3‐chloro‐5‐(trifluoromethyl)‐2‐acetonitrile pyridine (8.63 g) as a yellow oily liquid with a yield of 81% and a purity of 96%.

[0039] A...

Embodiment 2

[0041] The preparation method of fluopyram of the present embodiment has the following steps:

[0042] 2,3-Dichloro-5-trifluoromethylpyridine (10.0 g, 46.5 mmol), potassium hydroxide (2.6 g, 46.5 mmol) were added to dimethylsulfoxide (50 mL). Ethyl cyanoacetate (5.25 g, 46.5 mmol) was added dropwise to the above mixture at room temperature. After the dropwise addition was complete, the reaction was reacted at 70° C. for 3 hours. After the reaction was completed, it was cooled to room temperature. The pH was adjusted to 2-3 with hydrochloric acid, and the reaction solution was stirred at 160° C. for 13 hours. The reaction solution was cooled to room temperature, adjusted to pH 8-9 with 30% potassium hydroxide solution, and extracted with ethyl acetate. The organic phase was concentrated and then distilled under reduced pressure to obtain 3-chloro-5-(trifluoromethyl)-2-acetonitrile pyridine (8.5 g) as a yellow oily liquid with a yield of 79% and a purity of 95%.

[0043] Add...

Embodiment 3

[0045]The preparation method of fluopyram of the present embodiment has the following steps:

[0046] 2,3-Dichloro-5-trifluoromethylpyridine (10.0 g, 46.5 mmol), potassium carbonate (9.6 g, 70.0 mmol) were added to dimethylsulfoxide (70 mL). Methyl cyanoacetate (6.93 g, 70.0 mmol) was added dropwise to the above mixture at room temperature. After the dropwise addition was complete, the reaction was carried out at 80° C. for 2 hours. After the reaction was completed, it was cooled to room temperature. The pH was adjusted to 2-3 with hydrochloric acid, and the reaction solution was stirred at 160° C. for 14 hours. The reaction solution was cooled to room temperature, adjusted to pH 8-9 with 30% potassium hydroxide solution, and extracted with ethyl acetate. The organic phase was concentrated and distilled under reduced pressure to obtain 3‐chloro‐5‐(trifluoromethyl)‐2‐acetonitrile pyridine (8.84 g), a yellow oily liquid with a yield of 83% and a purity of 96%.

[0047] Add 3...

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Abstract

The invention relates to a fluopyram preparation method, which sequentially comprises: (1) carrying out a substitution reaction on 2,3-dichloro-5-trifluoromethylpyridine and ethyl cyanoacetate or methyl cyanoacetate at a temperature of 30-160 DEG C in the presence of an alkali and a solvent, adjusting the reaction liquid to an acidic pH value after completing the reaction, and carrying out a decarboxylation reaction at a temperature of 80-160 DEG C to obtain 3-chloro-5-(trifluoromethyl)-2-acetonitrilepyridine; and (2) carrying out tandem hydrogenation and condensation reaction on the 3-chloro-5-(trifluoromethyl)-2-acetonitrilepyridine prepared in the step (1) and o-trifluoromethylbenzoyl chloride at a temperature of 20-100 DEG C in the presence of a catalyst, hydrogen, an alkali and a solvent to obtain fluopyram. According to the present invention, the preparation method has the short steps, avoids the unnecessary protection-deprotection step, is economical and environmentally friendly, and is suitable for industrial production.

Description

technical field [0001] The invention specifically relates to a preparation method of fluopyram. Background technique [0002] Fluopyram is a new type of benzamide fungicide with high efficiency and low toxicity. It inhibits mitochondrial respiration by blocking the electron transfer of succinate dehydrogenase in the respiratory chain. Its broad-spectrum bactericidal spectrum can be applied to a variety of diseases of more than 70 kinds of crops. Whether it is used alone or in combination, it shows a good control effect. It is mainly used to control gray mold, powdery mildew, Late blight, downy mildew, and rice blast have great development potential in the pesticide market. [0003] At present, the preparation of fluopyram mainly contains the following routes: [0004] Route 1: [0005] [0006] The route uses 2,3-dichloro-5-trifluoromethylpyridine, diethyl malonate and o-trifluoromethylbenzoic acid as starting materials, and the final product fluopyram is obtained thro...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 安静刘玉超周炜周志豪吴天宇
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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