Method for reducing 1,3,4-triazole substituent in 1,2,4-triazole alkylation reaction process

An alkylation reaction and triazolidine technology, which is applied in the field of reducing 1,3,4-triazolidine substitutes in the process of 1,2,4-triazolidine alkylation, can solve the problem of poor yield. It can shorten the reaction time, simplify the operation and reduce the reaction temperature.

Active Publication Date: 2019-12-13
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

The former requires a large amount of solvent for purification and has a large loss, while t

Method used

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  • Method for reducing 1,3,4-triazole substituent in 1,2,4-triazole alkylation reaction process

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0023] Example 1

[0024] The synthesis of tebuconazole: 1,2,4-triazole (17.44g, 252.5mmol), sodium hydroxide (10.4g, 259.9mmol), triethylbenzyl ammonium chloride 2.8g, N, N- 10g of dimethylformamide was put into the reaction flask, and after preheating to 80°C, 2-(4-chlorophenethyl)-2-tert-butyloxirane (59.1g, 247.5mmol) was added dropwise. When the temperature is controlled at ≤95°C, after the dropwise addition is completed, it is kept at 98-102°C for 2-3 hours. After the heat preservation is completed, water is added to separate the layers, and the organic layer is washed with water until the pH<8. After the organic layer is desolvated under negative pressure, the obtained Tebuconazole finished product 74.5g, content 97.8%, yield 95.6%.

Example Embodiment

[0027] Example 2

[0028] Synthesis of epoxiconazole: 2-bromomethyl-2-(4-fluorophenyl)-3-(2-chlorophenyl)-oxirane (58.1g, 170.02mmol), 1,2,4 -Triazole (12.9g, 187.0mmol), sodium hydride (4.6g, 190.42mmol) and tetramethylammonium chloride 2.3g were placed in a reaction flask, heated to 70°C and stirred for 1-2 hours, then cooled after the reaction was complete Bring to room temperature, add water to separate layers, wash and dry the organic layer with water, saturated sodium chloride solution, and water successively, and desolvate under reduced pressure to obtain 53.8 g of epoxiconazole, with a content of 97.2% and a yield of 93.3%.

Example Embodiment

[0031] Example 3

[0032] Synthesis of epoxiconazole: 2-methylsulfonate-2-(4-fluorophenyl)-3-(2-chlorophenyl)-oxirane (69.31g, 194.3mmol), 1, 2,4-Triazole (14.1g, 204.0mmol), sodium hydride (5.4g, 223.4mmol) and 1.2g of tetrabutylammonium bromide were dissolved in 5g of DMF, heated to 60°C and stirred for 1-2 hours, and the reaction was complete After cooling to room temperature, adding water to separate layers, the organic layer was washed with water, saturated sodium chloride solution, and water successively and dried. After precipitation under reduced pressure, 60.8 g of epoxiconazole was obtained, with a content of 97.3% and a yield of 92.3%.

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Abstract

The invention relates to a method for reducing a 1,3,4-triazole substituent in 1,2,4-triazole alkylation reaction process. The method comprises the steps that 1, 2, 4-triazole and an alkylation reagent are subjected to an alkylation reaction in the presence of an alkali and a catalyst, after the reaction is finished, 1, 2, 4-triazole substituent is obtained through aftertreatment, and the catalystis one or a combination of more of polyether, cyclic crown ether, quaternary ammonium salt, quaternary phosphorus salt, quaternary ammonium base and tertiary amine. The method is simple to operate; the method is wide in application range, the content of the 1, 3, 4-triazole substituent in the alkylation reaction process can be reduced, the yield of the 1, 2, 4-triazole substituent is increased, the reaction time is shortened, the reaction temperature is reduced, solvent use is reduced or avoided, the resource utilization rate is increased, three wastes are reduced, the production cost is reduced, and the method meets the requirements of a green and environment-friendly process.

Description

technical field [0001] The present invention specifically relates to a method for reducing 1,3,4-triazole substituents during the alkylation reaction of 1,2,4-triazole. Background technique [0002] Compounds with 1,2,4-triazole as the active structural component have strong biological activity and are widely used in the fields of pesticides and medicines. In the field of pesticides, triazole pesticides show good antibacterial effects In addition, it can also regulate the physiological performance of plants, change the binding group and have both insecticidal and herbicidal activities. [0003] 1,2,4-triazole substitutes are usually obtained by alkylating 1,2,4-triazole with an alkylating agent. During the reaction, the 1,3,4-triazole substitutes Formation is unavoidable, and its content varies with the type of alkylating agent. 1,2,4-triazole substitutes and 1,3,4-triazole substitutes have the following structures respectively: [0004] [0005] In order to obtain hig...

Claims

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Application Information

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IPC IPC(8): C07D249/08C07D405/06
CPCC07D249/08C07D405/06
Inventor 陈佳姜宇华周炜蔡军义丁菲
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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