Preparation method of boscalid

A technology of boscalid and formamide, applied in the field of compound synthesis, can solve problems such as high cost and environmental harm, and achieve the effects of low cost, reduced environmental damage, and less three wastes

Active Publication Date: 2021-12-24
上海埃农生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of organic bases is much more expensive than the use of inorganic bases, and most of the organic bases are highly volatile, which is harmful to the environment

Method used

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  • Preparation method of boscalid
  • Preparation method of boscalid
  • Preparation method of boscalid

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preparation example Construction

[0069] One of the objects of the present invention is to provide a preparation method of boscalid, characterized in that, comprising the following steps:

[0070] 1) making biphenyl-2-formic acid and an acyl chloride reagent carry out acyl chloride reaction to obtain biphenyl-2-formyl chloride;

[0071] 2) making the biphenyl-2-formyl chloride obtained in step 1) undergo an amidation reaction with an amidating reagent to obtain biphenyl-2-formamide;

[0072] 3) making the biphenyl-2-carboxamide obtained in step 1) react with chlorine gas in the presence of a catalyst to obtain 4'-chloro-2-biphenylcarboxamide;

[0073] 4) the 4'-chloro-2-biphenylcarboxamide obtained in step 3) is subjected to a Hoffman rearrangement reaction to obtain 4'-chloro-2-aminobiphenyl;

[0074] 5) The resulting 4'-chloro-2-aminobiphenyl is condensed with 2-chloronicotinyl chloride in the presence of an inorganic base to obtain boscalid.

[0075] Each step of the preparation method of the present inve...

Embodiment 1

[0129] Embodiment 1: the synthesis of biphenyl-2-formic acid

[0130] At room temperature, 9-fluorenone (750 grams), potassium hydroxide (375 grams) and toluene (3700 milliliters) of 90% purity were added in the reaction flask, and the reaction flask was placed in a thermal oil bath and heated to about 105° C. The internal temperature suddenly began to rise violently automatically and rose to 124°C in about 20 seconds, and a large amount of foam was formed. The temperature was maintained at 120°C, the toluene was refluxed, and the reaction was carried out for 1 hour. After the completion of the reaction was monitored by thin-layer chromatography (TLC), the reaction system was cooled to about 50°C, water (4000 ml) was added to the reaction system, the phases were extracted and separated, the aqueous phase was collected, adjusted to PH≈3 with hydrochloric acid, and precipitated A large amount of white solid was centrifuged and dried to obtain biphenyl-2-carboxylic acid (819 g, p...

Embodiment 2

[0131] Embodiment 2: the synthesis of biphenyl-2-formic acid

[0132] 9-Fluorenone (750 g) was dissolved in toluene (1800 mL) at room temperature. Add potassium hydroxide (375 grams) and toluene (1800 milliliters) with a purity of 90% into the reaction flask at room temperature, heat it to about 105° C., and add the above-mentioned 9-fluorenone dropwise to the reaction flask with a constant pressure dropping funnel. Toluene solution, the dropwise addition time is about 20 minutes. Keep the temperature at 105°C and react for 9h. After TLC monitors that the reaction is over, cool the reaction system to about 50°C, add water (4000 ml) to the reaction system, extract and separate the phases, collect the water phase, adjust to PH ≈ 3 with hydrochloric acid, and precipitate a large amount of white solid. After separation and drying, biphenyl-2-carboxylic acid (813 g, purity 99%, yield 98.5%) was obtained. MS: [M - =197.1]

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Abstract

The invention relates to a preparation method of boscalid, and correspondingly relates to a preparation method of intermediates 4 '-chloro-2-biphenylformamide and 4'-chloro-2-aminobiphenyl. The method comprises the following steps: taking 9-fluorenone as a raw material, carrying out ring opening, acyl chloride substitution, amidation, chlorination and Hofmann rearrangement degradation to obtain 2-(4 '-chlorophenyl) aniline, and condensing the 2-(4'-chlorophenyl) aniline and 2-chloronicotinamide to obtain the product boscalid. According to the method disclosed by the invention, the target product can be obtained at high yield and high purity, and the harm to the environment can be reduced while the cost is reduced.

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to a preparation method of boscalid. Background technique [0002] Boscalid is a nicotinamide fungicide developed by BASF in Germany. It is mainly used to prevent and control powdery mildew, gray mold, various rots, brown rots and root rots. It was approved in the UK in 2004. , Germany and Switzerland are registered as pesticide fungicides. Boscalid belongs to the succinate coenzyme Q reductase inhibitor in the mitochondrial respiratory chain, which has a strong inhibitory ability to spore germination and has no cross-resistance with other fungicides. [0003] The synthesis methods described in prior art documents, such as patent documents 1 to 3, all use expensive palladium metal catalysts, and the use of palladium catalysts will inevitably increase the synthesis and production costs significantly. Moreover, in these documents, a large amount of organic bases are use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82C07C231/12C07C233/65C07C209/56C07C211/52
CPCC07D213/82C07C51/60C07C231/02C07C231/12C07C209/56C07C63/331C07C233/65C07C211/52
Inventor 鲁喜成李云龙徐国俊
Owner 上海埃农生物科技有限公司
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