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Benzotriazole compounds and a preparing method thereof

A technology for benzotriazole and compounds, which is applied in the field of organic compound synthesis, can solve the problems of complex operation of benzotriazole compounds and insufficient mild reaction conditions, and achieve the effects of simple post-processing, convenient operation and high reaction efficiency

Inactive Publication Date: 2018-05-15
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Purpose of the invention: the first technical problem to be solved by the present invention is the problem of complex operation in the preparation process of benzotriazole compounds
[0009] The second technical problem to be solved by the present invention is the problem that the reaction conditions are not mild enough in the preparation process of benzotriazole compounds

Method used

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  • Benzotriazole compounds and a preparing method thereof
  • Benzotriazole compounds and a preparing method thereof
  • Benzotriazole compounds and a preparing method thereof

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preparation example Construction

[0037] A kind of preparation method of benzotriazole compound, take o-phenylenediamine or o-phenylenediamine compound and tert-butyl nitrite as raw materials with the structure shown in formula (I), through intramolecular The diazotization reaction obtains the benzotriazole compound shown in formula (II);

[0038] Above-mentioned reaction process, available following reaction equation expression:

[0039]

[0040] (1) The molar ratio of o-phenylenediamine or o-phenylenediamine compound and t-butyl nitrite of structure shown in the formula is 1:(1~5), preferably 1:(1~3).

[0041] (1) O-phenylenediamine or o-phenylenediamine compounds

[0042] O-phenylenediamine or o-phenylenediamine compound has the structure shown in formula (I):

[0043]

[0044] In formula (I), each R is independently selected from H, chlorine, bromine, trifluoromethyl, tert-butyl and methyl.

[0045] (2) Reaction solvent

[0046] The reaction solvent used in the present invention is dimethyl sulfo...

Embodiment 1

[0061] Synthesis of Benzotriazole

[0062]

[0063] At room temperature, o-phenylenediamine (0.3mmol, 1equiv) and tertbutyl nitrite (0.45mmol, 1.5equiv) were added to the reaction tube, and 50mmol of H 2 O, stirred at 25°C reaction temperature for 15min, and the reaction solution was obtained after the reaction; then the reaction solution was cooled and extracted with 10ml of ethyl acetate to obtain ethyl acetate containing the extract; then the ethyl acetate containing the extract was obtained by adding Excessive anhydrous sodium sulfate was dried, filtered, and concentrated under reduced pressure to obtain a concentrate; finally, the concentrate was separated by column chromatography (using 300 mesh silica gel), using petroleum ether and ethyl acetate at a volume ratio of 3:1 as the eluent, The eluent was collected, and the solvent was spun off to obtain a white solid, that is, the benzotriazole compound represented by formula (II), with a yield of 99%.

[0064] The data...

Embodiment 2

[0072] Synthesis of 5,6-dichlorobenzotriazole

[0073]

[0074] At room temperature, 4,5-dichloro-o-phenylenediamine (0.3 mmol, 1 equiv) and tertbutyl nitrite (1.5 mmol, 5 equiv) were added to the reaction tube, and 300 mmol of H 2 O, stirred at 40°C reaction temperature for 30min, and the reaction solution was obtained after the reaction was completed; then the reaction solution was cooled and extracted with 10ml of ethyl acetate to obtain ethyl acetate containing the extract; then the ethyl acetate containing the extract was obtained by adding Excessive anhydrous sodium sulfate was dried, filtered, and concentrated under reduced pressure to obtain a concentrate; finally, the concentrate was separated by column chromatography (using 400 mesh silica gel), using petroleum ether and ethyl acetate at a volume ratio of 3:1 as the eluent, The eluate was collected, and the solvent was spun off to obtain a white solid, that is, the benzotriazole compound represented by formula (II...

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Abstract

The invention relates to benzotriazole compounds and a preparing method thereof. o-phenylenediamine or an o-phenylenediamine compound n-butyl nitrite are adopted as reaction raw materials and are subjected to an intramolecular diazo-reaction at room temperature in a reaction solvent to obtain the corresponding benzotriazole compound. According to the method, the range of substrates is wide, reaction conditions are mild, after-treatment is simple, and a product yield and quality are high. A novel synthesis route and method for the benzotriazole compounds are developed. The benzotriazole compounds have good application potentials and research value.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a benzotriazole compound and a preparation method. Background technique [0002] Benzotriazole (BTA) is an important class of organic synthesis intermediates, mainly used as water treatment agents, preservatives and light stabilizers, and used in antirust oils, fats, copper and copper alloys and other products. For example: in electroplating, it is used to purify silver, copper and zinc on the surface, and it has anti-tarnish effect. BTA is a good ultraviolet light absorber, which can stabilize products sensitive to ultraviolet light, such as preventing diazo dyes from fading, and treating thin products such as paper, woven fabrics, films, and metal coins with BTA can prevent discoloration. In the machining process, adding BTA to grinding oil and cutting oil can make the processed copper parts not change color. The product can also be used as an a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/18
CPCC07D249/18
Inventor 蔡悦铭刘妙昌张鑫徐雨婷杨烨翡毕康黄小波高文霞吴华悦
Owner WENZHOU UNIVERSITY
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