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Preparation method of 4,5-diphenyl substituted triazole compound

A technology of diphenyl and compound, which is applied in the field of preparation of 4,5-diphenyl substituted triazole compounds, and can solve problems such as harsh reaction conditions

Active Publication Date: 2019-03-08
山东亘元新材料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above methods all need to use explosive sodium azide, and the reaction conditions are harsh

Method used

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  • Preparation method of 4,5-diphenyl substituted triazole compound
  • Preparation method of 4,5-diphenyl substituted triazole compound
  • Preparation method of 4,5-diphenyl substituted triazole compound

Examples

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Embodiment 1

[0020] The preparation of embodiment 1 biological carbon load base

[0021] (1) Take Ginkgo biloba (200g), wash and dry to constant weight, 2 In the presence of the presence, the temperature was raised to 800°C at a rate of 10°C / min, and after carbonization for 3 hours, the temperature was lowered to room temperature to obtain biochar;

[0022] (2) Get the biochar (10g) obtained in step (1) and soak it with sodium hydroxide solution (6mol / L, 100mL) for 12 hours, wash with water, and dry to obtain the biochar-loaded alkali (hereinafter referred to as product A, figure 1 ).

Embodiment 2

[0024] Get the biochar (10g) obtained in step (1) of Example 1 and soak it with potassium hydroxide solution (4mol / L, 150mL) for 12 hours, wash and dry to obtain the biochar-loaded alkali (hereinafter referred to as product B, and figure 1 consistent).

Embodiment 3

[0025] Example 3 Preparation of 4,5-diphenyl-2H-1,2,3-triazole

[0026] Dissolve benzaldehyde (2mmol) in absolute ethanol (20mL), add anhydrous hydrazine (2.4mmol), heat to reflux temperature and react for 6 hours, add benzonitrile (1.6mmol) and product A (20mg), continue After reflux reaction for 5 hours, product A was recovered by filtration. After the filtrate was concentrated, it was diluted with chloroform, washed with water and saturated sodium chloride successively, dried over anhydrous sodium sulfate, filtered and concentrated, and subjected to silica gel column chromatography (200-300 mesh silica gel ), using petroleum ether / ethyl acetate (15:1-10:1) as an eluent to obtain 329 mg of a white solid, which is 4,5-diphenyl-2H-1,2,3-triazole compound, The yield is about 92.9%. 1 H NMR (CDCl 3 ,400MHz), δ:12.82(br s,1H),7.54(d,J=3.3Hz,4H),7.38-7.36(m,6H). 13 C NMR (CDCl 3 ,100MHz), δ:142.8,130.4,128.7,128.6,128.3.HRMS (such as figure 2 ).

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Abstract

The invention relates to a preparation method of a 4,5-diphenyl substituted triazole compound. The preparation method comprises the following steps: enabling a compound shown as in a formula I in thedescription and anhydrous hydrazine to react for 5-6 hours in absolute ethyl alcohol at the reflux temperature, adding cyanobenzene and a biochar loaded alkali, continuing to implement the reflux reaction for 4-5 hours, and obtaining the 4,5-diphenyl substituted triazole compound with a structure II, wherein R1 is chosen from C1-C3 alkyl, C1-C3 alkoxy, halogen and the like, n is an integer from 0to 5, the molar ratio of the compound shown in the formula I to the anhydrous hydrazine to the cyanobenzene is 1:(1.2-1.5):(0.8-1.0), and the use level of the biochar loaded alkali is that 10-15 mg ofthe biochar loaded alkali is used for each millimole of the compound shown as in the formula I.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of a 4,5-diphenyl substituted triazole compound. Background technique [0002] The triazole structure is an important group in biologically active compounds and an important structure of many chemical and pharmaceutical intermediates. Triazole compounds exhibit a variety of biological activities in medicine, pesticides, etc., especially in agricultural fungicides. At present, there are more than 20 kinds of triazole fungicides that have been commercialized. The synthesis methods of triazole compounds mainly include the following: (1) preparation by reaction of alkynes and sodium azide; (2) preparation by reaction of benzaldehyde, nitromethane and sodium azide. The above methods all need to use explosive sodium azide, and the reaction conditions are harsh. Therefore, it is difficult to develop a method for preparing triazoles without using sodium...

Claims

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Application Information

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IPC IPC(8): C07D249/06B01J23/04
CPCB01J23/04C07D249/06
Inventor 陈华进
Owner 山东亘元新材料股份有限公司
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