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Preparation method of prothioconazole

A technology of prothioconazole and heterogeneous oxidation, applied in the direction of organic chemistry, etc., can solve the problems of large amount of solvent, low product yield, unreusable oxidant, etc., and achieves easy large-scale production and realizes recycling. Effect

Active Publication Date: 2018-10-23
JIANGXI TIANYU CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] At present, the existing preparation methods all have the defects of low product yield, large amount of solvent, and oxidant that cannot be reused. Therefore, how to develop a new synthetic method is of great significance and value for the industrial production of prothioconazole

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  • Preparation method of prothioconazole
  • Preparation method of prothioconazole
  • Preparation method of prothioconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] At room temperature, 10.0 g (99.4% purity, 28.7 mmol) of 2-(1-chloro-cyclopropan-1-yl)-1-(2-chloro-phenyl)-3-(4,5-bis Hydrogen-1,2,4-triazolidine-5-thiocarbon-1-yl)-propan-2-ol, 30g toluene and 35.0g (66.0mmol) ferric chloride aqueous solution were added to a 250mL four-necked flask and stirred evenly , and then the temperature was raised to between 30-40° C., and the reaction progress was monitored by HPLC. After the reaction was completed, the temperature was lowered to 10-20° C., and 8.5 g of solids were obtained after suction filtration and drying. HPLC analysis showed that the solid contained 98.1% of 2-(1-chloro-cyclopropan-1-yl)-1-(2-chloro-phenyl)-3-(4,5-dihydro-1,2, 4-triazol-5-thiocarbon-1-yl)-propan-2-ol. Therefore, the calculated yield is 83.9% of the theoretical value (this yield is the yield after the first batch of reactions, and after the organic phase is reused, the yield is 99%). The filtrate was separated into layers to obtain 22.5 g of an organic ...

Embodiment 2

[0040]At room temperature, 10.0 g (99.4% purity, 28.7 mmol) of 2-(1-chloro-cyclopropan-1-yl)-1-(2-chloro-phenyl)-3-(4,5-bis Hydrogen-1,2,4-triazolidine-5-thiocarbon-1-yl)-propan-2-ol, 22.5g of the organic phase recovered in Example 1, 7.5g of fresh toluene and 35.0g (66.0 mmol) the aforementioned regenerated ferric chloride aqueous solution was added into a 250mL four-neck flask and stirred evenly, then the temperature was raised to 30-40°C, and the reaction progress was monitored by HPLC. After the reaction was completed, the temperature was lowered to 10-20° C., suction filtered and dried to obtain 9.94 g of solid. HPLC analysis showed that the solid contained 98.5% of 2-(1-chloro-cyclopropan-1-yl)-1-(2-chloro-phenyl)-3-(4,5-dihydro-1,2, 4-triazol-5-thiocarbon-1-yl)-propan-2-ol. Therefore, the calculated yield was 99.0% of theory. The filtrate was separated into layers to obtain 23.0 g of an organic phase and 35.0 g of an aqueous phase. The organic phase can be used dire...

Embodiment 3

[0043] At room temperature, 10.0 g (99.4% purity, 28.7 mmol) of 2-(1-chloro-cyclopropan-1-yl)-1-(2-chloro-phenyl)-3-(4,5-bis Hydrogen-1,2,4-triazolidine-5-thiocarbon-1-yl)-propan-2-ol, 25.0g chlorobenzene and 35.0g (66.0mmol) ferric chloride aqueous solution were added to a 250mL four-necked flask Stir evenly, then heat up to 30-40°C, and monitor the reaction progress by HPLC. After the reaction was completed, the temperature was lowered to 10-20° C., and 8.7 g of solids were obtained after suction filtration and drying. HPLC analysis showed that the solid contained 98.0% of 2-(1-chloro-cyclopropan-1-yl)-1-(2-chloro-phenyl)-3-(4,5-dihydro-1,2, 4-triazol-5-thiocarbon-1-yl)-propan-2-ol. Therefore, the calculated yield was 86.3% of theory. The filtrate was separated into layers to obtain 22.0 g of an organic phase and 34.5 g of an aqueous phase. The organic phase can be used directly as a solvent for the next batch of oxidation reactions.

[0044] A small amount of concentra...

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Abstract

The invention provides a preparation method of prothioconazole. The preparation method comprises the steps that a compound shown in the formula I and ferric chloride are subjected to a heterogeneous oxidizing reaction in an aromatic hydrocarbon solvent, and prothioconazole is obtained. The preparation method provided by the invention makes the amount of the solvent in the reaction be less by usingthe independent aromatic hydrocarbon solvent, by mass ratio, the using amount of the solvent is 1-6 times of the mass of the raw material, prothioconazole is more easily to produce in large scales, and the target product with the content being 98.0% or above is obtained directly through filtration and drying, the processes of extraction and desolvation are omitted, industrialized production is facilitated, and the production cost is lowered.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a preparation method of prothioconazole. Background technique [0002] Prothioconazole (2-(1-chloro-cyclopropan-1-yl)-1-(2-chloro-phenyl)-3-(4,5-dihydro-1,2,4-triazole- 5-thiol-1-yl)-propan-2-ol) is a new type of broad-spectrum triazolethione fungicide developed by Bayer, mainly used to prevent and control many diseases of cereals, wheat and bean crops, Prothioconazole has low toxicity, no teratogenicity and mutagenicity, no toxicity to embryos, and is safe to humans and the environment. At present, its synthesis method mainly contains the following several kinds: [0003] CN1411450A discloses a preparation method: 2-(1-chloro-cyclopropan-1-yl)-1-(2-chloro-phenyl)-3-(4,5-dihydro-1,2, 4-Triazolidin-5-thiocarbon-1-yl)-propan-2-ol is reacted with aqueous hydrochloric acid solution of ferric chloride, and the selected diluent is one of ethyl acetate, ethanol or a mixture of toluene a...

Claims

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Application Information

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IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 王淼丁亚伟陆成樑
Owner JIANGXI TIANYU CHEM CO LTD
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