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A method for preparing 1,2,3-thiadiazole-5-carboxamide compounds

A technology for formamides and compounds, applied in the fields of chemical industry and compound preparation, can solve the problems of increased production costs, a large amount of waste water, affecting product quality, etc., and achieve the effects of reducing the amount of "three wastes", reducing production costs, and reducing difficulty

Active Publication Date: 2020-08-04
LIER CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The object of the invention of the present invention is: for existing reports, the 1,2,3-thiadiazole-5-carboxamide compounds with the structure of formula I are all obtained through 4-methyl[1,2,3]thiadiazole Oxadiazole-5-formyl chloride and 2-aminothiazoles are obtained by reacting in the presence of an acid-binding agent (such as triethylamine), and the salt generated by the acid-binding agent and hydrogen chloride must be recovered, resulting in increased production costs and large amounts of Waste water affects product quality and aggravates the difficulty of post-treatment, providing a method for preparing 1,2,3-thiadiazole-5-carboxamide compounds

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0028] Dissolve 5g (0.05mol) 2-aminothiazole in 57g toluene, heat to 100°C under stirring, then add 8.53g (0.0525mol) 4-methyl[1,2,3]thiadiazole-5-methanol Acid chloride is added dropwise thereto at 100-105° C. under temperature control. After the dropwise addition is completed, the temperature of the mixture is raised to reflux for at least 4 hours to obtain a reaction mixture. Wherein, the hydrogen chloride gas released by the reaction is recovered by water or lye. After the reaction mixture was cooled, the reaction mixture was filtered at 0-10°C, the resulting filter cake was rinsed with a small amount of toluene, and dried to obtain 10.8g (yield: 90%) 4-methyl-N-(thiazole-2' -yl)-1,2,3-thiadiazole-5-carboxamide (LC purity: 97%).

Embodiment 2

[0030] Take 5.7g (0.05mol) of 2-amino-5-methylthiazole and suspend it in 114g of toluene, and heat it to 100°C under stirring to obtain the first solution. Then add 8.53g (0.0525mol) of 4-methyl[1,2,3]thiadiazole-5-formyl chloride dropwise into the first solution at 100-105°C under temperature control. After the dropwise addition is completed, the mixture is heated to reflux At least 4h, the reaction mixture was obtained. Wherein, the hydrogen chloride gas released by the reaction is recovered by water or lye. After the reaction mixture was cooled, the reaction mixture was filtered at 0-10°C, and the resulting filter cake was rinsed with a small amount of toluene, and dried to obtain 11.3g (yield: 94%) 4-methyl-N-(5'-formazan (thiazol-2'-yl)-1,2,3-thiadiazole-5-carboxamide (LC purity: 99%).

[0031] In addition, the applicant used 2-amino-5-methylthiazole in Example 2 with 2-amino-5-trifluoromethylthiazole, 2-amino-5-methylthiazole, 2-amino-4-phenyl Thiazole, 2-amino-4-(2',...

Embodiment 3

[0033] Dissolve 5.7g (0.05mol) of 2-amino-5-methylthiazole in 114g of dichloroethane, heat to 70°C under stirring, then add 8.53g (0.0525mol) of 4-methyl[1,2,3 ] Thiadiazole-5-formyl chloride was added dropwise at 70-75° C. under temperature control. After the dropwise addition was completed, the mixture was heated and refluxed for at least 4 hours to obtain a reaction mixture. The hydrogen chloride gas released by the reaction is recovered by water or lye. After the reaction mixture was cooled, the reaction mixture was filtered at 0-10°C, and the resulting filter cake was rinsed with a small amount of toluene, dried to obtain 8.7g (yield: 72%) 4-methyl-N-(5'- Methylthiazol-2'-yl)-1,2,3-thiadiazole-5-carboxamide (LC purity: 96%).

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Abstract

A method of preparing 1,2,3-thiadiazole-5-formamide compounds is disclosed. The objective of the method is to overcome a problem that 1,2,3-thiadiazole-5-formamide compounds are prepared by reacting 4-methyl[1,2,3]thiadiazole-5-formyl chloride with 2-aminothiazole type compounds under the existence of an acid-binding agent (such as triethylamine) in present reports, and a salt generated by the acid-binding agent and hydrogen chloride must be recovered so that after-treatment difficulty is increased. The inventor in an experiment process unexpectedly found that: under certain reaction conditions, and without the need of adding any acid-binding agent, the 4-methyl[1,2,3]thiadiazole-5-formyl chloride and the 2-aminothiazole type compounds having structures shown as a formula II can be reacted to obtain the 1,2,3-thiadiazole-5-formamide compounds shown as a formula I in high yields. In the method, no acid-binding agent is added, and therefore a plurality of difficulties in product-salt separation are overcome at one stroke, and the 1,2,3-thiadiazole-5-formamide compounds shown as the formula I and having high purity can be obtained through a very simple after-treatment manner.

Description

technical field [0001] The invention relates to the field of chemical engineering, especially the field of compound preparation, and specifically relates to a method for preparing 1,2,3-thiadiazole-5-carboxamide compounds. Background technique [0002] The structural formula of 1,2,3-thiadiazole-5-carboxamides is shown in formula I below: [0003] [0004] Among them, R 1 and R 2 independently selected from hydrogen, alkyl, halogen substituted alkyl or m is a number from 1 to 4, each R 3 are independently hydrogen, halogen, alkyl, or halogen-substituted alkyl. [0005] 1,2,3-thiadiazole-5-carboxamide compounds are a class of substances that can improve plant disease resistance, and their synthesis methods and uses in plant protection have been patented by CN1810808, CN100420686, CN101020687, CN101343269, CN101544633, etc. as reported. [0006] From the synthetic methods of published reports, the 1,2,3-thiadiazole-5-carboxamide compounds with the structure of formul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12
CPCC07D417/12
Inventor 吴锋李宏王玉华程柯
Owner LIER CHEM CO LTD