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Double-triazole substituted ethoxy benzene compound and preparation method and application thereof

A technology of diethoxybenzene and diethoxyphenyl, which is applied in the field of synthesis of ethoxybenzene compounds, can solve problems such as unretrieved and undetected, and achieve high reaction yield, high purity, high The effect of applying the foreground

Inactive Publication Date: 2015-08-12
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, 4-(4-((4H-1,2,4-triazol-4-yl)methyl)2,5-diethoxyphenyl)-4H-1,2, The compound 4-triazole, not to mention 4-(4-((4H-1,2,4-triazol-4-yl)methyl)2,5-diethoxyphenyl) -4H-1,2,4-Triazole compound reported in the literature

Method used

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  • Double-triazole substituted ethoxy benzene compound and preparation method and application thereof
  • Double-triazole substituted ethoxy benzene compound and preparation method and application thereof
  • Double-triazole substituted ethoxy benzene compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] The preparation method of 1,4-bis(bromomethyl)-2,5-diethoxybenzene (compound I) is as follows:

[0034] (1) Add p-bromophenol (1.10 g, 10 mmol), ethyl bromide (2.26 mL, 30 mmol), sodium hydroxide (1.10 g, 10 mmol), 20 mL of methanol, and reacted at 60°C for three hours. After the reaction, the reaction system was lowered to room temperature, poured into water, and a large amount of precipitate was precipitated. After suction filtration, the filter cake was collected and recrystallized with 95% ethanol to obtain 1 , 4-diethoxybenzene, yield 91%; melting point 71-72 ° C.

[0035](2) Add 1,4-diethoxybenzene (1.66 g, 10 mmol), paraformaldehyde (0.75 g , 25 mmol), potassium bromide (2.98 g, 25 mmol), 20 mL of glacial acetic acid, 5 mL of concentrated sulfuric acid was slowly added dropwise through a constant pressure dropping funnel, and reacted at 60°C for six hours. After the reaction, the reaction system was Cool down to room temperature, pour into water, precipitate a ...

Embodiment 2

[0037] The preparation method of 3-(1H-1,2,4-triazol-1-yl)propionitrile (compound II) is as follows:

[0038] Add 1H-1,2,4-triazole (1.38 g, 20 mmol) and 20 mL of toluene to a 50 mL single-necked flask equipped with a magnet, reflux condenser and constant pressure dropping funnel, and add acrylonitrile dropwise (1.31mL, 20mmol), refluxed for 20 hours, after the reaction, the reaction system was lowered to room temperature, and the toluene was removed to obtain 3-(1H-1,2,4-triazol-1-yl)propionitrile. The rate is 89%. The melting point is 35-36°C.

Embodiment 3

[0040] 4-(4-((4H-1,2,4-triazol-4-yl)methyl)2,5-diethoxyphenyl)-4H-1,2,4-triazole The preparation method is as follows:

[0041] Add 1,4-bis(bromomethyl)-2,5-diethoxybenzene (3.48 g, 10 mmol) into a 100 mL single-necked flask equipped with a magnet, reflux condenser and constant pressure dropping funnel, 3-(1H-1,2,4-triazol-1-yl)propionitrile (2.44 g, 20 mmol), 60 mL of acetonitrile, refluxed for 6 hours, distilled off the acetonitrile, added 1mol / L hydroxide Sodium aqueous solution 30mL, stirred at room temperature for 24 hours, extracted with dichloromethane, and the organic layer was washed with NaSO 4 Dry overnight, filter magnesium sulfate, and distill off dichloromethane to obtain 4-(4-((4H-1,2,4-triazol-4-yl)methyl)2,5-diethoxybenzene Base)-4H-1,2,4-triazole, yield 81%. Melting point 244-245°C;

[0042] 1 NMR (400 MHz, CDCl 3 ) : δ 8.19 (s, 4H), 6.68 (s, 2H), 5.13 (s, 4H), 4.01-3.94 (q, 4H), 1.43-1.39 (t, 6H).

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Abstract

The invention discloses a double-triazole substituted ethoxy benzene compound and a preparation method and application thereof. The organic compound is prepared by conducting reflux reaction on 1,4-bis (bromomethyl)-2,5-diethoxy benzene with 3-(1H-1,2,4-triazole-1-yl) propionitrile in acetonitrile, and then conducting basic hydrolysis. The preparation method of the present invention has the characteristics of simple operation, low production cost and little environmental pollution, and is applicable to large scale industrialization production. The compound prepared by the invention can be applied to the research on bactericide. The experimental results confirm that the double-triazole substituted ethoxy benzene compound has certain sterilization activity on Escherichia coli and Staphylococcus aureus, especially significant bactericidal activity against Staphylococcus aureus.

Description

[0001] This invention is supported by Tianjin Natural Science Foundation Key Project (12JCZDJC34300) and Tianjin Normal University School Development Fund (52XK1308). technical field [0002] The invention belongs to the technical field of organic synthesis and relates to the synthesis of bistriazole-substituted ethoxybenzene compounds. More specifically 4-(4-((4H-1,2,4-triazol-4-yl)methyl)2,5-diethoxyphenyl)-4H-1,2,4 - Triazole compound and its preparation method and application. Background technique [0003] Microorganisms are one of the main factors that cause diseases of animals and plants, among which fungi are the most harmful to plants. Most of the disease-preventing fungicides sold on the market today are fungal fungicides, and there are very few bacterial fungicides. The reason is that fungi have a wide range of harm to plants, so the economic losses and natural hazards they cause are also considerable. Now, triazole organic compound fungicides have attracted mo...

Claims

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Application Information

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IPC IPC(8): C07D249/08A01N43/653A01P1/00A61K31/4196A61P31/04A61P29/00
CPCA01N43/653C07D249/08Y02A50/30
Inventor 刘巨艳黄海静赵聪颖马恩忠
Owner TIANJIN NORMAL UNIVERSITY
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