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Preparation method of prothioconazole intermediate

A technology for prothioconazole and intermediates, which is applied in the field of preparation of fungicide prothioconazole intermediates, can solve the problems of increasing solid waste in reaction routes, increasing operation steps, etc., achieves less pollution of three wastes, simplifies operation steps, and saves The effect of high rate and content

Active Publication Date: 2017-08-15
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It not only increases the operation steps, but also increases the generation of solid waste in the reaction route

Method used

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  • Preparation method of prothioconazole intermediate

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Embodiment 1

[0033] The 2-(1-chloro-cyclopropan-1-yl)-1-(2-chlorophenyl)-2-hydroxyl-3-(1,2,4-triazolidine-5-thione of this embodiment The preparation method of -1-yl)-propane has the following steps:

[0034] Step (1), 2-(1-chlorocyclopropyl)-3-chloro-1-(2-chlorophenyl)-2-propanol I (28.0g, 0.10mol) was dissolved in acetonitrile (50mL) , followed by addition of potassium carbonate (13.8 g, 0.10 mol) and ethyl carbazate II (11.5 g, 0.11 mol). The reaction solution was stirred at 80°C for 4 hours. After the reaction, water (50 mL) was added to the reaction solution, followed by extraction with ethyl acetate (extraction three times, 50 mL each time), the organic phases were combined, dried over sodium sulfate and concentrated. 36.8 g of crude product was obtained, with a content of 83.4%. The obtained crude product was recrystallized from ethanol to obtain compound III (30.7 g), a pale yellow solid with a content of 95% and a yield of 84%. The NMR data of compound III are as follows:

[...

Embodiment 2

[0039] The 2-(1-chloro-cyclopropan-1-yl)-1-(2-chlorophenyl)-2-hydroxyl-3-(1,2,4-triazolidine-5-thione of this embodiment The preparation method of -1-yl)-propane has the following steps:

[0040] Step (1), 2-(1-chlorocyclopropyl)-3-chloro-1-(2-chlorophenyl)-2-propanol I (28.0g, 0.10mol) was dissolved in acetonitrile (50mL) , followed by addition of triethylamine (10.1 g, 0.10 mol) and ethyl carbazate II (11.5 g, 0.11 mol). The reaction solution was stirred at 80° C. for 3 hours. After the reaction, water (50 mL) was added to the reaction solution, followed by extraction with ethyl acetate (extraction three times, 50 mL each time), the organic phases were combined, dried over sodium sulfate and concentrated. 37.5 g of crude product was obtained, with a content of 86%. The obtained crude product was recrystallized from ethanol to obtain compound III (33.1 g), a pale yellow solid with a content of 95% and a yield of 91%.

[0041] Step (2), sodium hydroxide (3.60 g, 0.09 mol) ...

Embodiment 3

[0043] The 2-(1-chloro-cyclopropan-1-yl)-1-(2-chlorophenyl)-2-hydroxyl-3-(1,2,4-triazolidine-5-thione of this embodiment The preparation method of -1-yl)-propane has the following steps:

[0044] Step (1), 2-(1-chlorocyclopropyl)-3-chloro-1-(2-chlorophenyl)-2-propanol I (28.0g, 0.10mol) was dissolved in acetonitrile (50mL) , followed by the addition of triethylamine (10.1 g, 0.10 mol) and acetylhydrazide II (8.15 g, 0.11 mol). The reaction solution was stirred at 80° C. for 3 hours. After the reaction, water (50 mL) was added to the reaction solution, followed by extraction with ethyl acetate (extraction three times, 50 mL each time), the organic phases were combined, dried over sodium sulfate and concentrated. 36.3 g of crude product was obtained, with a content of 81%. The obtained crude product was recrystallized from ethanol to obtain compound III (30.0 g), a pale yellow solid with a content of 95% and a yield of 90%.

[0045] Step (2), potassium hydroxide (5.05 g, 0.0...

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Abstract

The invention relates to a preparation method of a prothioconazole intermediate. The method sequentially comprises the following steps: enabling a compound I and a compound II to react at the temperature of 20-120 DEG C in presence of a solvent; after the reaction is finished, treating to obtain a compound III; enabling the compound III to react with XOH, formaldehyde, YSCN and sodium hydrogen sulfate at the temperature of 10-80 DEG C in presence of a solvent so as to obtain a compound IV 2-(1-chloro-cyclopropyl-1-yl)-1-(2-chlorphenyl)-2-hydroxyl-3-(1,2,4-triazolidine-5-thioketone-1-yl)-propane, namely, the prothioconazole intermediate. Compared with the reported methods, the preparation method provided by the invention not only enables the intermediate to be more stable, but also reduces the amount of reagents, simplifies the operation steps, avoids the occurrence of side effects, increases the reaction efficiency and is less in pollution caused by the three wastes, thus being environmentally friendly and suitable for industrial production.

Description

technical field [0001] The present invention relates to the preparation method of bactericide prothioconazole intermediate, particularly 2-(1-chloro-cyclopropan-1-yl)-1-(2-chlorophenyl)-2-hydroxyl-3-(1 , The preparation method of 2,4-triazolidine-5-thiol-1-yl)-propane. Background technique [0002] Prothiaconazole (prothi°Conazole) is a low-toxicity, high-efficiency, broad-spectrum triazolethione fungicide developed by Bayer, mainly used to prevent and control many diseases of cereals, wheat and bean crops. 2-(1-Chloro-cyclopropan-1-yl)-1-(2-chlorophenyl)-2-hydroxy-3-(1,2,4-triazolidine-5-thione-1-yl )-propane (compound IV) is a key intermediate for the synthesis of prothioconazole. The synthesis of prothioconazole through this intermediate can not only avoid the generation of heterogeneous solid waste from the source, but also avoid a series of reaction conditions that are not suitable for industrial production, such as the use of dangerous chemicals and high temperatures...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 安静刘玉超周志豪褚小静顾怡
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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