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Method for preparing prothioconazole intermediate triazolidine derivative

A technology of triazolidine and prothioconazole, which is applied in the field of preparation of prothioconazole intermediate triazolidine derivatives, can solve the difficulty of separating the hydrochloride intermediate, increase the three wastes in the operation steps, and unfavorable industrial production, etc. problems, to achieve the effects of green and environmental protection in the reaction process, increase in reaction yield and product purity, and mild reaction conditions

Pending Publication Date: 2019-09-10
XINYI AGRI CHEM PLANT JIANGSU PROV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The hydrazine hydrochloride intermediate has many disadvantages such as difficult separation, serious corrosion to equipment, and difficulty in preservation. At the same time, it increases the operation steps and the generation of three wastes, which is not conducive to the progress of industrial production.

Method used

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  • Method for preparing prothioconazole intermediate triazolidine derivative
  • Method for preparing prothioconazole intermediate triazolidine derivative
  • Method for preparing prothioconazole intermediate triazolidine derivative

Examples

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preparation example Construction

[0028] The preparation method of the prothioconazole intermediate triazolidine derivative of this embodiment includes the following steps:

[0029] 1) Compound I: [2-(1-chloro-cyclopropane)-3-(2-chlorophenyl)-2-hydroxy]-propane-1-hydrazine in the presence of a solvent and inert gas at 0°C React with formaldehyde at ~80℃;

[0030] 2) The product obtained in step 1) continues to react with YSCN and sodium bisulfate to obtain compound II: 2-(1-chloro-cyclopropan-1-yl)-1-(2-chlorophenyl)-2-hydroxy- 3-(1,2,4-triazolidine-5-thio-1-yl)-propane, compound II is post-treated to obtain triazolidine derivatives;

[0031] The reaction formula is as follows:

[0032]

[0033] The post-treatment method is as follows: the obtained reaction liquid is washed with water and filtered to obtain the compound II triazolidine derivative.

[0034] In one embodiment, the solvent is water, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, dichloromethane, 1,2-dichloroethane, methyl acetate, ethyl acetat...

Embodiment 1

[0049] Combine [2-(1-chloro-cyclopropane)-3-(2-chlorophenyl)-2-hydroxy]-propane-1-hydrazine (compound Ⅰ) 10.17g (0.035mol) and 30g toluene under nitrogen protection After stirring to dissolve, add 3.02g (0.035mol) of aqueous formaldehyde solution, after stirring and reacting at 30℃ for 20min, add 2.84g (0.035mol) of sodium thiocyanate and 5.80g (0.042mol) of sodium bisulfate successively, and stir for reaction at 40℃ 3h, wash with water, stand for layering. After filtration and drying, a white solid 2-(1-chloro-cyclopropane-1-yl)-1-(2-chlorophenyl)-2-hydroxy-3-(1,2,4-triazolidine- 5-thio-1-yl)-propane 9.69 g (namely compound II, prothioconazole intermediate: triazolidine derivative), the content is 98%, and the yield is 78.5%.

Embodiment 2

[0051] Dissolve [2-(1-chloro-cyclopropane)-3-(2-chlorophenyl)-2-hydroxy]-propane-1-hydrazine 10.17g (0.035mol) and 40g xylene under nitrogen protection with stirring Then, 3.02g (0.035mol) of aqueous formaldehyde solution was added, and after stirring and reacting at 30°C for 40min, 2.84g (0.035mol) of sodium thiocyanate and 6.00g (0.05mol) of sodium bisulfate were added successively, stirred and reacted at 40°C for 6h, washed with water , Stand for layering. After filtration and drying, a white solid 2-(1-chloro-cyclopropane-1-yl)-1-(2-chlorophenyl)-2-hydroxy-3-(1,2,4-triazolidine- 5-thio-1-yl)-propane 9.89g, content 97.6%, yield 79.8%.

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Abstract

The invention discloses a method for preparing a prothioconazole intermediate triazolidine derivative. The method comprises the following steps: 1) in the presence of a solvent and an inert gas, enabling a compound I, namely [2-(1-chloro-cyclopropyl)-3-(2-chlorphenyl)-2-hydroxyl]-propyl-1-hydrazine to react with formaldehyde at 0-80 DEG C; 2) enabling the product obtained in the step 1) to continuously react with YSCN and sodium hydrogen sulfate so as to obtain a compound II, namely [2-(1-chloro-cycloprop-1-yl)-1-(2-chlorphenyl)-2-hydroxyl-3-(1,2,4-triazolidin-5-sulfur-1-yl)propane, and further carrying out post-treatment, so as to obtain the triazolidine derivative. When the method is adopted to prepare the compound II, a step of preparing a hydrazine dihydrochloride from the compound I is avoided, defects that a hydrazine hydrochloric acid intermediate is hard to separate, serious in equipment corrosion, hard to preserve, and the like, can be overcome, operation steps can be simplified, the reaction yield and the purity can be increased, and the method is applicable to industrial production.

Description

Technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for preparing prothioconazole intermediate triazolidine derivatives. Background technique [0002] Prothioconazole, chemical name (RS)-2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-di Hydrogen-1,2,4-triazole-3-thione is a broad-spectrum triazole fungicide developed by Bayer. It is mainly used to prevent and control many diseases such as cereals, wheat and beans. The pure product is white or light gray brown powdery crystals. The mechanism of action of prothioconazole is to inhibit the demethylation of lanosterol or 2,4-methylenedihydrolanosterol, the precursor of fungi, at the 14th position. Prothioconazole has good biological and ecological toxicity, and is safe for humans and the environment. [0003] Synthesis of 2-(1-chloro-cyclopropane-1-) by [2-(1-chloro-cyclopropane)-3-(2-chlorophenyl)-2-hydroxy]-propane-1-hydrazine (compound Ⅰ) Yl)-1-...

Claims

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Application Information

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IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 耿斌纪传武骆建张静
Owner XINYI AGRI CHEM PLANT JIANGSU PROV