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Method for preparing 2, 4-dichlorobenzoic acid from propiconazole 4-H isomer

A technology of dichlorobenzoic acid and propiconazole, which is applied in the field of synthesis of 2,4-dichlorobenzoic acid, can solve the problems of hazardous waste treatment, no disposal method, etc., achieves wide range of uses, reduces production costs, and reduces hazardous wastes Effect

Active Publication Date: 2022-07-29
ZHEJIANG BOSHIDA CROP TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] A large amount of propiconazole 4-H isomers will be produced during the condensation reaction of propiconazole. Liquid, there is no disposal method at present and can only be treated as hazardous waste

Method used

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  • Method for preparing 2, 4-dichlorobenzoic acid from propiconazole 4-H isomer
  • Method for preparing 2, 4-dichlorobenzoic acid from propiconazole 4-H isomer
  • Method for preparing 2, 4-dichlorobenzoic acid from propiconazole 4-H isomer

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Example 1: Synthesis of [2-chloro-4-(4-chlorophenoxy)-phenyl]-2-[1,2,4]triazole-4-ethanone

[0038]100 g (0.29 mol) of propiconazole 4-H isomer and 112 g (0.58 mol) of 19% hydrochloric acid were put into the reaction flask, the temperature was raised to 95° C., and the reaction was incubated for 18 hours.

[0039] In order to confirm the reaction product of this step, after the reaction is completed, the temperature is lowered to 25-30 ° C, the reaction solution is slowly added to a 15% aqueous sodium hydroxide solution, stirred for 1 hour, the pH is measured to be 11, filtered, and the obtained solid is dried , 72.1 grams of product were obtained, the content was 96.3% by liquid analysis, and the yield was 92.8%. The product was detected by liquid chromatography, and it was proved that the product was 1-(2,4-dichlorophenyl)-2-(4H- 1,2,4-Triazol-4-yl)ethanone, such as figure 2 shown.

Embodiment 2

[0040] Example 2: Synthesis of [2-chloro-4-(4-chlorophenoxy)-phenyl]-2-[1,2,4]triazole-4-ethanone

[0041] Same as Example 1, the difference is that 19% hydrochloric acid is replaced by 72% sulfuric acid, the temperature is raised to 140°C, and other conditions and process operations remain unchanged.

[0042] As a result, 70.1 g of 1-(2,4-dichlorophenyl)-2-(4H-1,2,4-triazol-4-yl)ethanone was obtained. Liquid phase analysis and detection confirmed that the product content was 96.8%, and the calculated yield was 90.7%.

Embodiment 3

[0043] Example 3: Synthesis of [2-chloro-4-(4-chlorophenoxy)-phenyl]-2-[1,2,4]triazole-4-ethanone

[0044] Same as Example 1, the difference is that 19% hydrochloric acid is replaced by 50% methanesulfonic acid (the molar weight is unchanged), and other conditions and process operations are unchanged.

[0045] As a result, 71.3 g of 1-(2,4-dichlorophenyl)-2-(4H-1,2,4-triazol-4-yl)ethanone was obtained. Liquid phase analysis and detection confirmed that the product content was 96.5%, and the calculated yield was 92%.

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Abstract

The invention relates to a method for preparing 2, 4-dichlorobenzoic acid from propiconazole 4-H isomer, which comprises the steps of hydrolysis reaction, substitution reaction and the like. According to the preparation method disclosed by the invention, the propiconazole 4-H isomer can be efficiently prepared into the 2, 4-dichlorobenzoic acid. The method can effectively reduce hazardous wastes, change wastes into valuables and reduce the production cost. The 2, 4-dichlorobenzoic acid prepared by the method is an intermediate of a bactericide piperidoxime, is also an intermediate of herbicides bensulfuron and pyrazolate, can be used for production of antimalarial drug altapine hydrochloride and non-mercuric diuretic tachycardia, can also be used as an intermediate of other medicines, dyes and pesticides, and has very wide application. The method provided by the invention can also provide a solution thought for conversion of triazole isomers of other medicines (such as itraconazole and intermediates thereof) or pesticides (such as ethoconazole and penconazole) and the like.

Description

【Technical field】 [0001] The invention relates to the synthesis of 2,4-dichlorobenzoic acid, in particular to a method for preparing 2,4-dichlorobenzoic acid from propiconazole 4-H isomer. 【Background technique】 [0002] Propiconazole is a systemic triazole fungicide with protective and therapeutic effects, which can be absorbed by roots, stems, and leaves, and can be quickly conducted upwards in plant strains to control ascomycetes, basidiomycetes and Diseases caused by deceitful fungi, especially for wheat take-all disease, powdery mildew, rust, root rot, rice fungus, and banana leaf spot have a good control effect. Vegetables have a good effect of controlling the growth and suppressing the seedlings. [0003] During the condensation reaction of propiconazole, a large amount of propiconazole 4-H isomers will be produced. After the propiconazole is extracted by conventional nitric acid salt formation, the obtained propiconazole 4-H isomers and their residues are separated....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/29C07C63/70
CPCC07C51/29C07D249/08C07C63/70Y02A50/30
Inventor 沈浩王海涛袁鸿威陈元元吴启超张宝华刘莹吴华龙
Owner ZHEJIANG BOSHIDA CROP TECH CO LTD
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