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Method for synthesising 1,5,9-trinitro-2,3,6,7,10,11-hexa-alkoxy triphenylene

A technology of hexaalkoxytriphenylene and a synthesis method, which is applied in the preparation of nitro compounds, organic chemistry and other directions, can solve the problems of many by-products, environmental pollution, and product yield of only 28%, and achieves simple operation and reaction The effect of mild conditions and high product yield

Inactive Publication Date: 2013-08-28
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
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Problems solved by technology

This method needs to be reacted under strong acidic and strong oxidative conditions, and the nitrogen oxides produced during the reaction will pollute the environment, and there are many by-products and the product yield is only 28%.

Method used

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  • Method for synthesising 1,5,9-trinitro-2,3,6,7,10,11-hexa-alkoxy triphenylene
  • Method for synthesising 1,5,9-trinitro-2,3,6,7,10,11-hexa-alkoxy triphenylene
  • Method for synthesising 1,5,9-trinitro-2,3,6,7,10,11-hexa-alkoxy triphenylene

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Experimental program
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Effect test

Embodiment 11

[0016] Synthesis of embodiment 11,5,9-trinitro-2,3,6,7,10,11-hexamethoxytriphenylene

[0017] Dissolve 0.51g (1.25mmol) of 2,3,6,7,10,11-hexamethoxytriphenylene in a flask filled with 10mL of chloroform, add 1.33g (7.5mmol) of benzenesulfonyl chloride, 1.27g of ( 7.5mmol) silver nitrate, the molar ratio of 2,3,6,7,10,11-hexamethoxytriphenylene to benzenesulfonyl chloride and silver nitrate is 1:6:6, stirred and reacted at 60°C for 48 hours, Then the reaction solution was cooled to room temperature, 10 mL of distilled water was added, extracted with chloroform (50 mL×3), and the organic phase was washed with saturated Na 2 CO 3 solution, washed with distilled water and anhydrous Na 2 SO 4 After drying, the product was separated and purified by silica gel column chromatography (trichloromethane eluent) to obtain a pale yellow solid 1,5,9-trinitro-2,3,6,7,10,11-hexamethoxy Triphenylene, its yield is 76%. The spectral data of the product are as follows:

[0018] IR (KBr) ν (...

Embodiment 21

[0022] Synthesis of Example 21,5,9-trinitro-2,3,6,7,10,11-hexamethoxytriphenylene

[0023] Dissolve 0.51g (1.25mmol) of 2,3,6,7,10,11-hexamethoxytriphenylene in a flask containing 10mL of chloroform, and add 1.66g (7.5mmol) of 4-nitrobenzenesulfonyl chloride , 1.27g (7.5mmol) silver nitrate, 2,3,6,7,10,11-hexamethoxytriphenylene and 4-nitrobenzenesulfonyl chloride, the molar ratio of nitrate in silver nitrate is 1:6:6 , stirred and reacted at 60°C for 24 hours, and the other steps were the same as in Example 1 to obtain light yellow solid 1,5,9-trinitro-2,3,6,7,10,11-hexamethoxytriphenylene, which was recovered The rate is 45%.

Embodiment 31

[0024] Synthesis of Example 31,5,9-trinitro-2,3,6,7,10,11-hexamethoxytriphenylene

[0025] Dissolve 0.51g (1.25mmol) of 2,3,6,7,10,11-hexamethoxytriphenylene in a flask filled with 10mL of o-dichlorobenzene, add 1.43g (7.5mmol) of 4-methylbenzenesulfonate Acyl chloride, 0.25g (1.50mmol) silver nitrate, 0.97g (3.00mmol) mercury nitrate, 2,3,6,7,10,11-hexamethoxytriphenylene and 4-methylbenzenesulfonyl chloride, mercury nitrate and nitric acid The molar ratio of nitrate in silver is 1:6:6, and the reaction is stirred at 60°C for 56 hours. The other steps are the same as in Example 1 to obtain a light yellow solid 1,5,9-trinitro-2,3,6,7 , 10,11-hexamethoxytriphenylene, the yield was 48%.

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Abstract

The invention discloses a method for synthesising 1,5,9-trinitro-2,3,6,7,10,11-hexa-alkoxy triphenylene. The method comprises the following step of synthesising 1,5,9-trinitro-2,3,6,7,10,11-hexa-alkoxy triphenylene by taking 2,3,6,7,10,11-hexa-alkoxy triphenylene as a raw material, and taking nitrate and alkyl sulfonyl chloride as nitration reagents. Compared with literature report methods, the method disclosed by the invention has the advantages of being moderate in reaction conditions, simple to operate, high in product yield, without the need of other strong acid reagents during a reaction process, and the like.

Description

technical field [0001] The invention belongs to the technical field of polycyclic condensed aromatic hydrocarbons containing four rings, in particular to a method for synthesizing 1,5,9-trinitro-2,3,6,7,10,11-hexaalkoxy substituted triphenylene Compound synthesis method. Background technique [0002] 1,5,9-Trinitro-2,3,6,7,10,11-hexaalkoxytriphenylene (Formula Ⅰ) is an important intermediate for the synthesis of triazepines. Triazepine compounds can be used as organic optoelectronic materials in optoelectronic devices, and have important application value in organic field effect diodes, solar cells, light emitting diodes and other devices. [0003] [0004] At present, 1,5,9-trinitro-2,3,6,7,10,11-hexaalkoxytriphenylene uses fuming nitric acid as a nitrating reagent, and 2,3,6,7,10, Synthesized from 11-hexaalkoxytriphenylene. For example, using 2,3,6,7,10,11-hexamethoxytriphenylene as raw material, fuming nitric acid (98%) as nitrating reagent, and a mixture of dichlor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/37C07C201/08
Inventor 魏俊发常健董叶叶苏汉勇张强刘大勇
Owner SHAANXI NORMAL UNIV
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