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Diphenyl sulfide compound displaced with double triazole and preparing method and application thereof

A technology of thioether compounds and compounds, which is applied in the field of bis(4-(1H-1,2,4-triazol-1-yl)phenyl) sulfide compounds, can solve the problem of unretrieved, unfounded, etc. problem, to achieve the effect of large profit margin, simple and easy reaction operation, and suitable for large-scale industrial production

Inactive Publication Date: 2015-10-07
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the compound bis(4-(1H-1,2,4-triazol-1-yl)phenyl)sulfide has not been found, let alone any related bis(4-(1H-1,2, 4-triazol-1-yl) phenyl) sulfide synthesis method reported in the literature

Method used

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  • Diphenyl sulfide compound displaced with double triazole and preparing method and application thereof
  • Diphenyl sulfide compound displaced with double triazole and preparing method and application thereof
  • Diphenyl sulfide compound displaced with double triazole and preparing method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0044] The molar ratio of bis(4-bromophenyl)sulfide:triazole:potassium carbonate:copper oxide is 2:10:30:1

[0045]Add CuO (0.0398 mg, 0.5 mmol), potassium carbonate (2.0731 g, 15 mmol), triazole (0.345 mg, 5 mmol), bis( 4-bromophenyl)sulfide (0.344g, 1 mmol), 20 mL DMF. Start stirring at 100oC and react for 24 hours. After the reaction, the reaction liquid was lowered to room temperature, filtered, and 100 mL of water was added to the filtrate, and a large amount of precipitate was precipitated, filtered with suction, and the filter cake was collected, with a yield of 78.8%.

Embodiment 2

[0047] Preparation:

[0048] The molar ratio of bis(4-bromophenyl)sulfide:triazole:potassium carbonate:copper oxide is 2:15:30:1

[0049] Add CuO (0.0398 mg, 0.5 mmol), potassium carbonate (2.0731 g, 15 mmol), triazole (0.345 mg, 5 mmol), bis( 4-bromophenyl)sulfide (0.344g, 1mmol), 20mL DMF. Start stirring and react at 150oC for 60 hours. After the reaction, the reaction solution was lowered to room temperature, filtered, and 100 mL of water was added to the filtrate, and a large amount of precipitate was precipitated, filtered with suction, the filter cake was collected, and recrystallized with water to obtain bis(4-(1H-1,2,4-triazole- 1-base) phenyl) sulfide compound yield 78.8%. image 3 It is the H NMR spectrum of bis(4-(1H-1,2,4-triazol-1-yl)phenyl)sulfide compound.

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Abstract

The invention discloses a diphenyl sulfide compound displaced with double triazole and a preparing method and application thereof. 'One pot method' is adopted, in other words, bi(4-bromophenyl)thioether, 1,2,4-triazole , potassium carbonate and copper oxide are heated to prepared the organic compound. The molar ratio among the double (4-bromophenyl) thioether, the triazole comprising the first azole, the second azole and the fourth azole, the potassium carbonate and the copper oxide is 2:10-1:5:30:1. The reaction temperature ranges from 70 DEG C to 210 DEG C, and the reaction time ranges from 24 hours to 120 hours. The preparing method has the advantages of being simple in technological operating, low in cost, low in environmental pollution, and suitable for industrial production in a large-scaled mode. The double (4-(1H-triazole comprising the first azole, the second azole and the fourth azole-1-group) phenyl) thioether compound can be applied to the researching aspect of a sterilizing agent.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a bis(4-(1H-1,2,4-triazol-1-yl)phenyl)sulfide compound and a preparation method thereof. Bis(4-(1H-1,2, Application of 4-triazol-1-yl)phenyl)sulfide in the preparation of fungicides. At the same time, the present invention is funded by Tianjin Natural Science Foundation Key Project (12JCZDJC34300) and Tianjin Normal University Development Fund (52XK1308). Background technique [0002] A large number of microorganisms exist in our lives, they constantly threaten people's health, cause corruption, deterioration and decomposition of various materials, endanger industrial and agricultural production and the natural environment, and cause huge economic losses. At present, the most effective way to kill microorganisms is to use chemical agents. Bis(4-(1H-1,2,4-triazol-1-yl)phenyl) sulfide fungicide has both high-efficiency bactericidal effect and The damage to body tissue and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08A01N43/653A01P1/00
CPCC07D249/08A01N43/653
Inventor 刘巨艳张鑫
Owner TIANJIN NORMAL UNIVERSITY
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