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Method for preparing azide compound through azidation based on C-H activated anilines

A compound and nitrogen source technology, applied in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve problems such as harsh conditions, reduce the progress of azide compounds, environmental pollution, etc., and achieve the effect of simple operation process

Inactive Publication Date: 2017-05-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional methods for the azidation of anilines generally have harsh conditions and cause a certain degree of pollution to the environment. These problems have greatly reduced the progress of the research on azides.

Method used

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  • Method for preparing azide compound through azidation based on C-H activated anilines
  • Method for preparing azide compound through azidation based on C-H activated anilines
  • Method for preparing azide compound through azidation based on C-H activated anilines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Preparation of 2-azidoaniline (2-azidoaniline)

[0035]

[0036] Add 0.5mmol of aniline (1a) into 4mL of water, add 0.125mmol of copper acetate, 1.0mmol of sodium azide, and 1.0mmol of hydrogen peroxide, and react at room temperature for 2 hours. After the reaction, add saturated NaCl aqueous solution to the reaction solution , extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness at 60° C. under reduced pressure to obtain the crude compound represented by the formula (2a). The crude compound represented by formula (2a) was subjected to silica gel column chromatography, and a solution with a volume ratio of ethyl acetate and petroleum ether of 1:5 was used as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was tracked and collected by TLC. The obtained eluate was desolventized under reduced pressure and dried to obtain 42 mg of the pure compound represented by formula (2a), with a ...

Embodiment 2

[0039] Preparation of 2-azido-3-bromoaniline (2-azido-3-bromoaniline)

[0040]

[0041] Add 0.5mmol m-bromoaniline (1b) into 4mL of water, add 0.125mmol copper acetate, 1.0mmol sodium azide, 1.0mmol hydrogen peroxide, and react at room temperature for 2 hours. After the reaction, add saturated NaCl aqueous solution was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness at 60°C under reduced pressure to obtain the crude compound represented by the formula (2b). The crude compound represented by formula (2b) was subjected to silica gel column chromatography, and the solution with a volume ratio of ethyl acetate and petroleum ether of 1:8 was used as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was tracked and collected by TLC. The obtained eluent was desolventized under reduced pressure and dried to obtain 69 mg of the pure compound represented by formula (2b), with a yield of 65%.

...

Embodiment 3

[0044] Preparation of 2-azido-3-chloroaniline (2-azido-3-chloroaniline)

[0045]

[0046] Add 0.5mmol m-chloroaniline (1c) to 4mL of water, add 0.125mmol copper acetate, 1.0mmol sodium azide, 1.0mmol hydrogen peroxide, and react at room temperature for 2 hours. After the reaction, add saturated NaCl aqueous solution was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness at 60°C under reduced pressure to obtain the crude compound represented by the formula (2c). The crude compound represented by formula (2c) was subjected to silica gel column chromatography, using a solution with a volume ratio of ethyl acetate and petroleum ether of 1:6 as the mobile phase, and followed by TLC to collect the eluent with an Rf value of 0.3-0.5, and collected The obtained eluent was desolventized under reduced pressure and dried to obtain 55 mg of the pure compound represented by formula (2c), with a yield of 66%.

...

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Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a method for preparing an azide compound through azidation based on C-H activated anilines. The method comprises the following steps: by using anhydrous copper acetate as a reaction catalyst and hydrogen peroxide as an oxidant, adding an aniline compound and sodium azide into water, reacting for two hours at a room temperature, extracting by using ethyl acetate, and carrying out vacuum concentration, thus obtaining a corresponding organic azide coarse product; carrying out column chromatography separation and purification, thus obtaining a corresponding pure product. The method disclosed by the invention has the characteristics that the operation is simple, the reaction conditions are gentle, the reaction time is short, and the method is green and environment-friendly.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a method for preparing azide compounds by catalyzing aromatic ammonia and its application in biological activity. Background technique [0002] Azide compounds contain azido-based high-energy active functional groups, which are an important class of organic synthesis intermediates and have been widely used in organic synthesis, chemical biology, functional materials and clinical medicine and other fields. Aniline (Aniline) is one of the most important amine substances, mainly used in the manufacture of dyes, drugs, resins, etc., can be used as raw materials for pharmaceutical sulfonamides, and is also an intermediate for the production of spices, plastics, varnishes, films, etc.; As a stabilizer in explosives, as an anti-knock agent in gasoline, and as a solvent, etc. The traditional methods for the azidation of anilines generally have harsh conditions and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/00C07C247/16C07D211/88C07D215/40
CPCC07B43/00C07C247/16C07D211/88C07D215/40
Inventor 朱勍方红梨付曼琳顾晓旭
Owner ZHEJIANG UNIV OF TECH
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