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A kind of preparation method of fenpyrazone

A technology for toxazone and preparation process, applied in the field of organic compound preparation, can solve the problems of high price, high reaction yield and high cost, and achieve the effects of being beneficial to industrial production, high product yield and realizing localization

Active Publication Date: 2019-09-20
HUNAN HAILI CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Adachi H et al. [US 6147031A1, 2000-11-14], Zhang Dayong et al. [CN 103788083 A, 2014-05-14] and Shen Yunhe et al. [CN 104693195 A, 2015-06-10] adopted this route, respectively with 2 , 3-dimethyl-4-(methylsulfonyl)benzoic acid methyl ester, 1,2-dimethyl-3-nitrobenzene and 3-[3-bromo-2-methyl-6-(methyl sulfonyl)phenyl]-4,5-dihydroisoxazole is used as raw material to synthesize fenpyrazone, but there are problems such as raw material is not easy to get, low yield, high cost, etc., so it is not suitable for industrialized production
[0010] Both routes require the use of 1-methyl-5-hydroxypyrazole, which can be prepared from 2-(ethoxymethylene)diethyl malonate or 3-methoxymethyl acrylate and monomethyl Hydrazine reaction preparation, but the reaction of 2-(ethoxymethylene) diethyl malonate and monomethylhydrazine has problems such as complicated operation and low yield; 3-methoxymethyl acrylate and monomethylhydrazine The reaction yield is high, the price of methyl 3-methoxyacrylate and monomethylhydrazine is expensive, and there are problems such as high production cost
[0011] The relevant patents of fenpyrazone have not yet expired, so there is no report on industrial production in China, and all products are monopolized sales

Method used

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  • A kind of preparation method of fenpyrazone

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Embodiment 1

[0041] A preparation method of fenpyrazone of the present invention, comprising the following steps:

[0042] (1) Synthesis of compound (VII)

[0043] Add 86.5g (0.4mol) of 2-(ethoxymethylene)diethyl malonate into a three-necked flask, cool to below 30°C, and add 112g (containing 0.8mol of NH 3 ·H 2 O) mass fraction is 25% ammoniacal liquor. After the addition, the temperature of the reaction system was lowered to 5°C, and 25 g (containing 0.4 mol of N 2 h 4 ·H 2 O) The mass fraction is 80% hydrazine hydrate. After the addition is complete, the reaction solution is heated to 60° C. and stirred for 4 hours. After the reaction is completed, cool to below 10° C., and slowly add 81 g (containing 0.8 mol HCl) concentrated hydrochloric acid dropwise to neutralize the aqueous ammonia. It was then extracted with ethyl acetate, dried over anhydrous sodium sulfate, and desolventized to obtain 55.7 g of a light yellow solid with a yield of 89.2%. LC-MS (m / z): 157.1 (M+H + ); 1 H...

Embodiment 2

[0055] A preparation method of fenpyrazone of the present invention, comprising the following steps:

[0056] (1) Synthesis of compound (VII)

[0057] Add 92.1g (0.4mol) of 2-(methoxymethylene)dipropyl malonate into a three-necked flask, cool to below 30°C, and add dropwise 56g (0.4mol) of mass fraction below 30°C under temperature control. 25% ammonia water. After the addition, the temperature of the reaction system was lowered to 0° C., and 37.5 g (0.6 mol) of 80% hydrazine hydrate was added dropwise under heat preservation. After the addition, the temperature of the reaction solution was raised to 80° C. and stirred for 3 hours. After the reaction is completed, cool to below 10° C., and slowly add 40.5 g (containing 0.4 mol HCl) concentrated hydrochloric acid dropwise to neutralize the aqueous ammonia. Then it was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and desolventized to obtain 59.6 g of a light yellow solid with a yield of 87.5%.

[0058] (...

Embodiment 3

[0069] A preparation method of fenpyrazone of the present invention, comprising the following steps:

[0070] (1) Synthesis of compound (VII)

[0071] Add 103.3g (0.4mol) of 2-(methoxymethylene) di-tert-butyl malonate into a three-necked flask, cool to below 30°C, and add 168g (1.2mol) of mass fraction dropwise under temperature control below 30°C 25% ammonia water. After the addition, the temperature of the reaction system was lowered to 5 °C, and 37.5 g (0.6 mol) of 80% hydrazine hydrate was added dropwise under heat preservation. After the addition, the temperature of the reaction solution was raised to 40 °C and stirred for 6 hours. After the reaction was completed, cool to below 10° C., and slowly add 121.5 g (containing 1.2 mol HCl) concentrated hydrochloric acid dropwise to neutralize the aqueous ammonia. It was then extracted with ethyl acetate, dried over anhydrous sodium sulfate, and desolventized to obtain 65 g of a light yellow solid with a yield of 88.2%.

[00...

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Abstract

The invention discloses a preparation method of topramezone. The particularly comprises the steps of carrying out cyclization, methylation, hydrolysis, amidation, Grignard reaction, oxidation and demethylation on 2-(alkoxymethylene)malonate as a raw material, so as to obtain a target product, wherein the yield of the target product reaches 61.8%-63.2%. According to the preparation method, the raw materials such as a palladium / platinum catalyst which is high in cost and difficult to recycle, a virulent rearrangement catalyst and high-cost methylhydrazine are not adopted, and the preparation method which is low in cost, easy in operation, low in pollution and accordant with large-scale industrial production requirements is provided.

Description

technical field [0001] The invention relates to the technical field of preparation of organic compounds, in particular to a preparation method of fenpyrazone. Background technique [0002] The trade names of fenpyrazone include Convey, Impact, Clio, Baowei, etc. It is a new type of high-efficiency herbicide developed by BASF in Germany. Pyrazenone is the first active ingredient in pyrazolone compounds, which can be absorbed by roots, young stems and leaves, and conduct to the top and base of the plant to the meristem, and inhibit plastoquinone biogenesis. The 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) in the synthesis, indirectly affects the synthesis of carotenoids, interferes with the synthesis and function of chloroplasts, and finally leads to severe albinism (due to the degradation of chlorophyll). Among the herbicides for post-emergence stem and leaf treatment of corn fields currently on the market, pyrenzazone is the safest herbicide for corn fields. It is safe for ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/10
Inventor 罗先福全春生李萍周锦萍刘国文臧阳陵
Owner HUNAN HAILI CHEM IND
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