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Method for synthesizing 1, 2, 4-triazole-3-carboxylic acid methyl ester

A technology of methyl carboxylate and triazole, which is applied in the synthesis of five-membered nitrogen-containing heterocycles and the field of synthesizing 1,2,4-triazole-3-methyl carboxylate, can solve the problem of difficult to achieve and impossible to carry out. Problems such as industrial production and environmental protection problems of diethyl oxalate method are difficult to deal with

Active Publication Date: 2020-10-23
TUOXIN GROUP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the particularly unpleasant smell during the thiolation process, it is impossible to carry out industrial production in production
[0005] Among the above synthetic methods, the diazotization step needs to be carried out from the lime nitrogen method, and this reaction is more dangerous. The synthesis of the raw material of the ethyl cyanoformate method needs to use highly toxic sodium cyanide, which is difficult to realize, while the diethyl oxalate method needs to be carried out. The environmental issues of the thiogenation step are more difficult to deal with

Method used

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  • Method for synthesizing 1, 2, 4-triazole-3-carboxylic acid methyl ester
  • Method for synthesizing 1, 2, 4-triazole-3-carboxylic acid methyl ester
  • Method for synthesizing 1, 2, 4-triazole-3-carboxylic acid methyl ester

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Embodiment 1

[0028]

[0029] In the first step, add 200mL of methanol into the reaction bottle, cool down to 0°C and add 1.4g (0.01mol) of potassium carbonate, then keep the temperature of the reaction solution at 0-5°C, and slowly drop in 28.9g (0.2mol) of trichloroacetonitrile After the dropwise addition, the reaction was incubated for 20 minutes, and then a methanol solution of 12.0 g (0.2 mol) of formic hydrazide was added dropwise. After the dropwise addition, the temperature was raised to 25°C for 4 hours. At this time, a large amount of white solids precipitated out. The temperature was lowered to 10°C for suction filtration, and the filter cake was rinsed with a small amount of methanol. The collected filter cake was dried under reduced pressure to obtain 36.5 g (0.180 mol) of the addition intermediate 3. The yield is 90%.

[0030] In the second step, add the above-mentioned addition intermediate 3 (0.18mol) into the three-necked reaction flask, raise the temperature to 95°C unt...

Embodiment 2

[0033]

[0034] In the first step, add 200mL of methanol into the reaction bottle, cool down to 0°C and add 3.3g (0.01mol) of cesium carbonate, then keep the temperature of the reaction solution at 0-5°C, and then slowly drop in 28.9g (0.2mol) of trichloroacetonitrile After the dropwise addition, the reaction was incubated for 20 minutes, and then a methanol solution of 12.0 g (0.2 mol) of formic hydrazide was added dropwise. After the dropwise addition, the temperature was raised to 25°C for 4 hours. At this time, a large amount of white solids precipitated out. The temperature was lowered to 10°C for suction filtration, and the filter cake was rinsed with a small amount of methanol. The collected filter cake was dried under reduced pressure to obtain 37.5 g (0.181 mol) of the addition intermediate 3. The yield is 91%.

[0035] In the second step, add the above-mentioned addition intermediate 3 (0.181mol) into the three-necked reaction flask, raise the temperature to 95°C ...

Embodiment 3

[0038]

[0039] In the first step, add 200mL of ethanol to the reaction bottle, cool down to 0°C and add 1.4g (0.01mol) of potassium carbonate, then keep the temperature of the reaction solution at 0-5°C, and then slowly drop in 28.9g (0.2mol) of trichloroacetonitrile After the dropwise addition, the reaction was incubated for 20 minutes, and then an ethanol solution of 12.0 g (0.2 mol) of formic hydrazide was added dropwise. After the dropwise addition, raise the temperature to 25°C and react for 4 hours. At this time, a large amount of white solid precipitates out. Cool down to 10°C and filter with suction. The filter cake is rinsed with a small amount of ethanol. The collected filter cake is dried under reduced pressure to obtain 35.5 g (0.175 mol) of the addition intermediate 3. The yield is 87.5%.

[0040] In the second step, add the above-mentioned addition intermediate 3 (0.175mol) into the three-necked reaction flask, raise the temperature to 95°C until the solid me...

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Abstract

The invention discloses a method for synthesizing 1, 2, 4-triazole-3-carboxylic acid methyl ester, and belongs to the field of organic chemistry. The method comprises the following reaction steps: reacting trichloroacetonitrile 1 with formylhydrazine 2 to generate an intermediate 3, then carrying out cyclization reaction to obtain an intermediate 4, and finally carrying out alcoholysis reaction togenerate 1, 2, 4-triazole-3-carboxylic acid methyl ester 5. According to the method, only three steps of reaction are needed, the overall yield is high, dangerous diazotization deamination reaction in a traditional synthesis process is avoided, the safety risk in the reaction process is reduced, and meanwhile the production cost can be reduced.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to the synthesis of five-membered nitrogen-containing heterocyclic rings, in particular to a method for synthesizing methyl 1,2,4-triazole-3-carboxylate. Background technique [0002] Methyl 1,2,4-triazole-3-carboxylate, molecular formula C 4 h 5 N 3 o 2 , CAS: 4928-88-5, as a very important pharmaceutical intermediate, can be used to prepare antiviral and antitumor ribavirin and other drugs. The methods currently reported in the literature mainly fall into two categories: [0003] The first type: Synthesize with lime nitrogen as raw material, and obtain products through hydrazinolysis, condensation, esterification, deamination and other steps. The synthetic route of lime nitrogen as the starting material: lime nitrogen reacts with hydrazine hydrate to obtain the product of nitrile group addition, and then condenses with oxalic acid to obtain 1,2,4-triazole-3-carboxylate methyl es...

Claims

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Application Information

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IPC IPC(8): C07D249/10
CPCC07D249/10
Inventor 杨西宁王德地卫涛张赛楠胡琰琨李燕石田清
Owner TUOXIN GROUP
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