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Preparation method for fluazinam

A technology based on trifluoromethylpyridine and pyridyl, applied in the field of compound synthesis, can solve the problems of limited range of solvent selection, increase of waste water treatment cost, increase of alkali removal workload, etc., to suppress hydrolysis side reactions and benefit environmental protection , improve the effect of selectivity

Inactive Publication Date: 2018-12-04
江苏禾裕泰化学有限公司
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Problems solved by technology

On the one hand, the increase in the amount of alkali increases the workload of alkali removal in post-treatment; on the other hand, the choice of solvents is greatly limited
[0008] Furthermore, in the current production of fluazinam, post-treatment is usually done by adding a large amount of water to wash off the salt and unreacted alkali generated after the reaction, which will bring a large amount of waste water and increase the cost of waste water treatment
At the same time, since most of the solvents (such as tetrahydrofuran, etc.) used in industrial production are miscible with water, adding a large amount of water during post-treatment will also take away a large amount of solvent, so that the solvent cannot be effectively recycled, resulting in waste of resources

Method used

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preparation example Construction

[0034] A 3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluoro-2,6-dinitro-para The preparation method of toluidine, comprises the following steps:

[0035] (1) Make 2-amino-3-chloro-5-trifluoromethylpyridine and 2,4-dichloro-3,5-dinitrobenzotrifluoride in the presence of the first organic solvent, alkali and catalyst Specify the reaction temperature to react to obtain a reaction mixture;

[0036] (2) Purified 3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluoro- 2,6-Dinitro-p-toluidine.

[0037] In step (1), 2-amino-3-chloro-5-trifluoromethylpyridine is condensed with 2,4-dichloro-3,5-dinitrobenzotrifluoride, and its specific reaction formula is as follows:

[0038]

[0039] In step (1), relative to 1 mol of 2-amino-3-chloro-5-trifluoromethylpyridine, 1.0-1.2 mol of 2,4-dichloro-3,5-dinitrotrifluoro toluene. Preferably, 1.0-1.05 mol of 2,4-dichloro-3,5-dinitrobenzotrifluoride may be used relative to 1 mol of 2-amino-3-chloro-5-trifluoromethylp...

Embodiment 1

[0063] 200 g (i.e., about 1 mol) of 2-amino-3-chloro-5-trifluoromethylpyridine with a purity of 99%, 500 ml of acetonitrile, 1.5 g (i.e., about 0.004 mol) of ethylenediamine tetramine with a purity of 99% Disodium acetate Na 2 EDTA and 200g (that is, about 3.03mol) purity are 85% solid potassium hydroxide and drop into in the four-necked flask that is equipped with stirrer, thermometer and dropping funnel, open stirring and mix, be cooled to 0-5 ℃, then Add dropwise a solution containing 314.5g (i.e., about 1.03mol) of 2,4-dichloro-3,5-dinitrobenzotrifluoride and 500ml of acetonitrile with a purity of 99%, at a temperature of 0-5°C; After the addition was complete, the reaction was continued at 0-5°C for 3 hours.

[0064] After the reaction was completed, filter at normal temperature, and rinse the filter cake twice with acetonitrile, using 50ml of acetonitrile each time. After combining the obtained filtrate and eluent, it was neutralized to pH 6 with a small amount of 98% ...

Embodiment 2

[0066] 200g (i.e. about 1 mol) of 99% purity of 2-amino-3-chloro-5-trifluoromethylpyridine, 300ml of acetonitrile, 2.2g (i.e. about 0.097mol) of 99% purity of benzyl triethyl Ammonium chloride TEBA and 146g (that is, about 3.5mol) of solid sodium hydroxide with a purity of 96% are put into a four-necked flask equipped with a stirrer, a thermometer and a dropping funnel, and the stirring is started and mixed, cooled to 5- 10°C, then dropwise add a solution containing 305.3g (that is, about 1.00mol) of 2,4-dichloro-3,5-dinitrobenzotrifluoride and 200ml of acetonitrile with a purity of 99%, at a temperature of 5- 10°C; after the dropwise addition, continue the reaction at 5-10°C for 5 hours.

[0067] After the reaction was completed, filter at normal temperature, and rinse the filter cake twice with acetonitrile, using 50ml of acetonitrile each time. After combining the obtained filtrate and eluent, it was neutralized to pH 4 with a small amount of 98% concentrated sulfuric acid...

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Abstract

The invention discloses a preparation method for fluazinam. The method comprises the following steps: performing a reaction on 2-amino-3-chloro-5-trifluoromethylpyridine and 2,4-dichloro-3,5-dinitrobenzotrifluoride in the presence of a first organic solvent, an alkali and a catalyst at a specified reaction temperature to obtain a reaction mixture; and performing post treatment to obtain purified 3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridinyl)-alpha-alpha-alpha-trifluoro-2,6-dinitro-p-toluidine as a reaction product from the reaction mixture, wherein a catalyst is a phase transfer catalyst.According to the method disclosed by the invention, the phase transfer catalyst is added to the reaction, the reaction temperature is reduced, so that selectivity of the reaction is improved, an occurrence of a hydrolysis side reaction is inhibited, and a yield of the product is improved; and further, in the post treatment of the product, the alkali and the formed salt are removed by filtration and neutralization without water washing, and the alkali can be reused, so that generation of wastewater and waste of resources are reduced.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a preparation method of fluazinam. Background technique [0002] Fluazinamine (chemical name: 3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluoro-2,6-dinitro-p-methyl Aniline; English name: fluazinam; trade name: SHIRLAN, IKF-1216) is a new type of substituted aniline broad-spectrum fungicide developed by Japan Ishihara Industry Co. It also has good activity on diseases caused by fungi such as Phytophthora, Phytophthora, Plasmodium, Sclerotinia and Scabella. [0003] At present, the synthetic method of fluazinam mainly adopts compound A (2-amino-3-chloro-5-trifluoromethylpyridine) and compound B (2,4-dichloro-3,5-dinitrotrifluoro Toluene) under the effect of alkali and solvent, prepare fluazinam, concrete reaction equation is as follows: [0004] [0005] In this synthesis method, due to the presence of water in the solvent, compound B (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74
CPCC07D213/74
Inventor 岳晟顾建波
Owner 江苏禾裕泰化学有限公司
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