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Novel method for synthesizing 1,2,3-thiadiazole-5-formamidine compound

A technology of compound and target compound, which is applied in the field of synthesis of 1,2,3-thiadiazole-5-carboxamidine compounds, can solve the problems of large spatial position, low reactivity, complex components, etc., to reduce production costs, The effect of simple catalyst composition and environmental friendliness

Inactive Publication Date: 2015-04-22
XIHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The combined dehydration catalyst not only has complex components, but also has a high price, and at the same time, a large amount of phosphorus-containing wastewater is produced in the post-treatment process
At the same time, the patent (application number CN2015100098343) also analyzed that the main reason for using such a complex and highly active combined catalyst is because the target compound for the synthesis of reported TDCA is N-trisubstituted-1,2,3- Thiadiazole-5-carboxamidine compounds need to use compound B as a raw material, but the raw material compound B has a large steric position and low reactivity

Method used

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  • Novel method for synthesizing 1,2,3-thiadiazole-5-formamidine compound
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  • Novel method for synthesizing 1,2,3-thiadiazole-5-formamidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride (compound C ):

[0046] 1) Synthesis of ethyl carbazate:

[0047] Add 540ml (4.4mol) of diethyl carbonate and 255g (4mol) of 80% hydrazine hydrate into a 2000ml three-necked round bottom flask equipped with a condensing reflux tube, stir, and gradually raise the temperature to 50°C, the reaction system changes from turbid to clear liquid, keep the temperature and stir for 1 hour, lower to room temperature and continue to stir for 24 hours, distill ethanol and water under reduced pressure (remove the water brought in by ethanol and hydrazine hydrate), and dry in vacuum to obtain 399.2 g of white solid product, which is directly processed Next reaction.

[0048] 2) Synthesis of ethyl 3-(ethoxycarbonyl-hydrazone)butanoate

[0049] Add 508 mL (4 mol) of ethyl acetoacetate into a 2000ml three-neck flask, stir magnetically, and add 399.2 g of ethyl carbazate dropwise over 2 hours under ice water cooling (prepared ...

Embodiment 2

[0056] Synthesis of 2-amino-5-tert-butyl-1,3,4-thiadiazole (compound P ):

[0057] Add 109.4 g (1.20 mol) of thiosemicarbazide, 140 g (1.30 mol) of pivaloyl chloride, and 800 mL of toluene into a 2000 mL three-necked flask equipped with a thermometer and a stirring rod. Add 80 g (0.52 mol) of phosphorus oxychloride dropwise at 50°C, react at 70°C for 12 h, cool to room temperature, pour the reaction solution into an ice-water mixture, and separate to obtain 2-amino-5-tert-butyl- The toluene solution of 1,3,4-thiadiazole, the toluene solution was concentrated by distillation, cooled and recrystallized with a mixed solvent of ethyl acetate and cyclohexane to obtain gray solid 2-amino-5-tert-butyl-1,3,4 - Thiadiazole 152.8g, the liquid phase normalized purity is 98.8%, and the yield is 81%.

Embodiment 3

[0059] Synthesis of N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-methyl-1,2,3-thiadiazol-5-carboxamide (compound N ) (Equation 8):

[0060] Add 78.6 g of 2-amino-5-tert-butyl-1,3,4-thiadiazole (compound P ) (0.5mol), 600ml dichloromethane, 61.2g (0.6mol) triethylamine, stirring mechanically, controlling the temperature at -5~0°C, adding 85.6g (0.5mol) 4-methyl-1,2 dropwise ,3-Thiadiazole-5-carbonyl chloride (compound C ) and 300ml of dichloromethane solution. After the dropwise addition was completed, it was slowly raised to room temperature, and stirring was continued for 2 hours. Dichloromethane was removed under reduced pressure to obtain a solid, and the solid was washed with 2000ml of water, suction filtered and dried; the crude product of light yellow solid was obtained, and the crude product was recrystallized with toluene to obtain 107.7g of white solid, the yield was 76%, and the liquid phase normalized the purity 99.4%.

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Abstract

The invention discloses a novel method for synthesizing a 1,2,3-thiadiazole-5-formamidine compound. The target compound shown in general formula TDCA is prepared from a compound as shown in general formula M by virtue of a methylation reaction. The target component as shown in the general formula M is prepared from a compound as shown in general formula A and a compound as shown in general formula N by virtue of a condensation reaction, wherein during the methylation reaction, preferably, a catalyst is an organic metallic catalyst consisting of cuprous iodide and a ligand, namely 2,2,6,6-tetramethyl-3,5-heptadione; during the reaction, preferably, dimethylbenzene is taken as a solvent, and the optimum reaction temperature is 100-140 DEG C. The method disclosed by the invention is high in yield and more environment-friendly (as shown in Specification).

Description

technical field [0001] The present invention relates to a method for synthesizing 1,2,3-thiadiazole-5-carboxamidine compounds, in particular to a new synthesis method for 1,2,3-thiadiazole-5-carboxamidine compounds containing three nitrogen heterocycles . Background technique [0002] Amidines have a wide range of applications in medicine, and can be used as drugs for treating diabetes, cardiovascular diseases, anti-inflammatory drugs, anthelmintics and diuretics. Amidines are also widely used in agriculture. For example, the British Boots company has developed a new low-toxicity, broad-spectrum organic nitrogen acaricide with two amidine functional group structures, which has strong contact, fumigation and good penetration effects, and can be used for The prevention and treatment of ticks, mites, scabies, etc. parasitic on livestock has a good development prospect. [0003] Due to the wide application of amidines, especially in pharmaceuticals and pesticides, there are m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14
CPCC07D417/14
Inventor 刘萍杨维清马梦林张园园张燕
Owner XIHUA UNIV
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