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Synthesis method of 1,4-bis(p-toluenesulfonyl)trinitrocyclononane

A technology of benzoyl triazacyclononane and p-toluenesulfonyl group is applied in the field of synthesis of 1,4-bis-triazacyclononane, and can solve the problems of low reaction yield, low production efficiency, waste acid and the like, Achieve the effects of avoiding side reactions, low production costs, and simple process control

Pending Publication Date: 2021-08-20
仪征市海帆化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Both methods require a large amount of inorganic acid and organic acid, resulting in a large amount of waste acid; the reaction yield is low, the production efficiency is low, and it is not suitable for industrial production

Method used

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  • Synthesis method of 1,4-bis(p-toluenesulfonyl)trinitrocyclononane
  • Synthesis method of 1,4-bis(p-toluenesulfonyl)trinitrocyclononane
  • Synthesis method of 1,4-bis(p-toluenesulfonyl)trinitrocyclononane

Examples

Experimental program
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Effect test

Embodiment 1

[0026] In a 500ml four-necked flask equipped with an electric stirrer, a thermometer, a reflux condenser, and an oil bath heating pot, add 10g (0.018mol) of 1,4-bis(p-toluenesulfonyl)-7-benzoyl triazine Cyclononane, 5g (0.045mol) potassium tert-butoxide, 300ml tert-butanol, after adding the above materials, start to stir and heat up.

[0027] When the system was refluxed, start timing the heat preservation reaction. After 36 hours of heat preservation reaction, cool to room temperature and filter. The filter cake was washed with a large amount of water until the pH was neutral. The filter cake was dried to obtain 7.11 g. The liquid chromatography content is 96.75%, based on 1,4-bis(p-toluenesulfonyl)-7-benzoyltriazacyclononane, the molar yield is 90.39%.

Embodiment 2

[0029] In a 500ml four-necked flask equipped with an electric stirrer, a thermometer, a reflux condenser, and an oil bath heating pot, add 10g (0.018mol) of 1,4-bis(p-toluenesulfonyl)-7-benzoyl triazine Cyclononane, 3g (0.031mol) sodium tert-butoxide, 300ml tert-butanol, after adding the above materials, start to stir and heat up.

[0030] When the system was refluxed, start timing the heat preservation reaction. After 36 hours of heat preservation reaction, cool to room temperature and filter. The filter cake was washed with a large amount of water until the pH was neutral. The filter cake was dried to obtain 6.6 g. The liquid chromatography content is 95.17%, based on 1,4-bis(p-toluenesulfonyl)-7-benzoyltriazacyclononane, the molar yield is 83.91%.

Embodiment 3

[0032] In a 500ml four-necked flask equipped with an electric stirrer, a thermometer, a reflux condenser, and an oil bath heating pot, add 10g (0.018mol) of 1,4-bis(p-toluenesulfonyl)-7-benzoyl triazine Cyclononane, 20g (0.088mol) sodium ethoxide ethanol solution with a mass fraction of 30%, and 300ml of ethanol, after adding the above materials, start to stir and heat up.

[0033] When the system was refluxed, start timing the heat preservation reaction. After 12 hours of heat preservation reaction, cool to room temperature and filter. The filter cake was washed with a large amount of water until the pH was neutral. The filter cake was dried to obtain 3.2 g. The liquid chromatography content is 88.55%, based on 1,4-bis(p-toluenesulfonyl)-7-benzoyltriazacyclononane, the molar yield is 40.68%.

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Abstract

The invention discloses a synthesis method of 1,4-bis(p-toluenesulfonyl)trinitrocyclononane. The synthesis method comprises the following steps: with 1,4-bis(p-toluenesulfonyl)-7-benzoyltrinitrocyclononane as a substrate, removing a protecting group of a benzoyl group under an alkaline condition, and conducting a reaction under the condition that two p-toluenesulfonyl groups do not participate in the reaction so as to obtain the 1,4-bis(p-toluenesulfonyl)trinitrocyclononane. Reaction conditions are that a reflux reaction is adopted and reaction time is 10-36 hours. Compared with the prior art, the synthesis method of the invention has the following beneficial effects: the use of a large amount of inorganic acid and organic acid is avoided, and the problems of safety, environmental protection and the like are effectively guaranteed essentially; and reaction yield can be up to 90% or above.

Description

technical field [0001] The invention relates to a synthesis method of 1,4-bis(p-toluenesulfonyl)triazacyclononane. Background technique [0002] 1,4-bis(p-toluenesulfonyl)triazacyclononane, the molecular structure formula is: [0003] [0004] 1,4-bis(p-toluenesulfonyl)triazacyclononane is an important organic ligand intermediate. There is an unprotected amine group in its molecular structure, which can be connected to the required group, and then the p-toluenesulfonyl group is deprotected, and then connected to other asymmetric groups to obtain special-purpose organic compounds. body compound. [0005] At present, the synthetic method of 1,4-bis(p-toluenesulfonyl)triazacyclononane publicly reported is to synthesize 1,4,7-three(p-toluenesulfonyl)triazacyclononane by traditional method first, and then Under the condition of hydrogen peroxide or propionic acid, a p-toluenesulfonyl group is removed to obtain 1,4-bis(p-toluenesulfonyl)triazacyclononane. The synthetic rout...

Claims

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Application Information

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IPC IPC(8): C07D255/02
CPCC07D255/02Y02P20/55
Inventor 张燕邹从伟戴久坤周芬
Owner 仪征市海帆化工有限公司
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