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Benzotriazole compound synthesis method

A technology of benzotriazoles and synthesis methods, which is applied in the direction of organic chemistry, can solve the problems of not involving the structure of benzene rings, etc., and achieve the effect of changing optical and electrical properties, simple operation, and low cost

Inactive Publication Date: 2017-03-15
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the modification of this kind of benzotriazole compounds mainly focuses on the substituents on the N of the five-membered heterocycle, while the modification of the benzene ring structure is hardly involved.

Method used

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  • Benzotriazole compound synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Example 1: Preparation of 2-hexyl-benzo[d][1,2,3]triazole

[0022]

[0023] Add benzotriazole (10.00g, 83.94mmol), sodium tert-butoxide (8.47g, 105.77mmol) and n-bromohexane (16.21g, 98.21mmol) successively in a two-necked flask with a molar ratio of 1:1.17:1.26 , then add 100mL of methanol solution, the solution is heated to 80 ° C for 12 hours; stop the reaction, distill off the solvent methanol under reduced pressure to obtain the sample, and then dissolve the sample in dichloromethane, respectively, with deionized water and saturated saline Wash the dichloromethane solution, add anhydrous magnesium sulfate to dry the dichloromethane solution, filter and concentrate the dichloromethane solution, and the concentrated product is separated by silica gel chromatography (eluent is petroleum ether / dichloromethane, v / v= 2:1), and dried in vacuo to obtain 2-hexyl-benzo[d][1,2,3]triazole (7.20 g, 35.42 mmol) as a colorless liquid with a yield of 42%.

Embodiment 2

[0024] Example 2: Preparation of 2-hexyl-4,7-dibromo-benzo[d][1,2,3]triazole

[0025]

[0026] Dissolve 2-hexyl-benzo[d][1,2,3]triazole (3.45g, 16.97mmol) in 35mL of hydrobromic acid, raise the temperature to 100°C and stir at constant temperature for 1 hour, slowly drop into the molar ratio It is liquid bromine (15.46g, 96.72mmol) of 1:2.7, after dripping, it is heated to 135°C and refluxed at this temperature for 12 hours; to stop the reaction, add saturated aqueous sodium thiosulfate solution, extract with ethyl acetate, and use Wash the ethyl acetate solution with deionized water and saturated brine, add anhydrous magnesium sulfate to dry the ethyl acetate solution, filter and concentrate the ethyl acetate solution, and the concentrated product is separated by silica gel chromatography (eluent is petroleum ether / distillate Chloromethane, v / v=2:1), dried in vacuo to give light yellow liquid 2-hexyl-4,7-dibromo-benzo[d][1,2,3]triazole (4.90g, 13.57mmol) , and its yield w...

Embodiment 3

[0027] Example 3: Preparation of 2-hexyl-4,7-dibromo-5,6-dinitro-benzo[d][1,2,3]triazole

[0028]

[0029] Slowly drop 2-hexyl-4,7-dibromo-benzo[d][1,2,3]triazole (7.30g, 20.22mmol) into 60mL of mixed fuming nitric acid and concentrated sulfuric acid (fuming Nitric acid / concentrated sulfuric acid, v / v=1:1), keep the temperature of the reaction solution within 0°C, and stir for 3 hours; stop the reaction, pour the solution into ice water slowly, extract with ethyl acetate, and use deionized water and Wash the ethyl acetate solution with saturated brine, add anhydrous magnesium sulfate to dry the ethyl acetate solution, filter and concentrate the ethyl acetate solution, and the concentrated product is separated by silica gel chromatography (eluent is petroleum ether / dichloromethane, v / v=2:1), dried under vacuum to obtain light yellow solid 2-hexyl-4,7-dibromo-5,6-dinitro-benzo[d][1,2,3]triazole (5.7g , 12.64mmol), the yield was 62%.

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Abstract

The invention discloses a synthesis method of a sulfur alkyl substituted benzotriazole compound. The synthesis method includes the steps: taking benzotriazole as raw materials, and reacting the benzotriazole and alkyl bromide to obtain 2-hexyl-benzo[d] [1, 2, 3] triazole; brominating the 2-hexyl-benzo[d] [1, 2, 3] triazole to obtain 2-hexyl-4, 7-dibromo-benzo[d] [1, 2, 3] triazole; nitrating the 2-hexyl-4, 7-dibromo-benzo[d] [1, 2, 3] triazole to obtain 2-hexyl-4, 7-dibromo-5, 6-dinitro-benzo[d] [1, 2, 3] triazole; reacting the 2-hexyl-4, 7-dibromo-5, 6-dinitro-benzo[d] [1, 2, 3] triazole and 2-tributyltin thiophene to obtain 2-hexyl-4, 7-bithiophene-5, 6-dinitro-benzo[d] [1, 2, 3] triazole; reacting the 2-hexyl-4, 7-bithiophene-5, 6-dinitro-benzo[d] [1, 2, 3] triazole and the alkyl bromide to obtain the sulfur alkyl substituted benzotriazole compound. According to the synthesis method, raw materials are easy to obtain, cost is low, reaction conditions are mild, and sulfur alkyl is firstly introduced into benzotriazole.

Description

technical field [0001] The invention belongs to the technical field of chemical intermediate synthesis, and in particular relates to a synthesis method of benzotriazole compounds. Background technique [0002] Benzotriazole UV absorbers are additives that slow down the aging of polymer materials under sunlight, and can also be used in fine chemical products such as cosmetics, especially in automotive coatings. At present, the modification of this kind of benzotriazole compounds mainly focuses on the substituents on the N of the five-membered heterocycle, while the modification of the benzene ring structure is hardly involved. For the first time, we modified the parent structure of the benzene ring. Through chemical methods, we introduced alkylthio groups on the benzene ring, which changed the optical and electrical properties of benzotriazole in a large range. The synthesis method greatly expanded the benzotriazole compound. derivative. Contents of the invention [0003]...

Claims

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Application Information

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IPC IPC(8): C07D409/14
CPCC07D409/14
Inventor 海杰峰李玲韦刚林芝官
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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