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Synthesis method of 1,4-bis(p-toluenesulfonyl)-7-benzoyl trinitrocyclononane

A technology of benzoyl triazine and p-toluenesulfonyl, which is applied in the field of synthesis of 1,4-bis-7-benzoyl triazacyclononane, which can solve the problems of waste acid, low reaction yield and production efficiency Low-level problems, to achieve the effect of simple process control, avoid side reactions, and low production costs

Pending Publication Date: 2021-09-28
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)-7-benzoyl trinitrocyclononane
  • Synthesis method of 1,4-bis(p-toluenesulfonyl)-7-benzoyl trinitrocyclononane
  • Synthesis method of 1,4-bis(p-toluenesulfonyl)-7-benzoyl trinitrocyclononane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 2000ml four-necked flask equipped with an electric stirrer, a thermometer, a reflux condenser, and an oil bath heating pot, add 50g (0.097mol) N-benzoyl-O, O-p-toluenesulfonyl-diethanolamine, 37g (0.1mol) N,N'-bis(p-toluenesulfonyl)ethylenediamine, 500ml of toluene, 100ml of tap water, 45g (0.33mol) of anhydrous potassium carbonate, after adding the above materials, start to stir and heat up.

[0026] When the temperature rose to 90°C, the system boiled and there was reflux in the reflux condenser. Timing heat preservation and reflux, after heat preservation for 5 hours, after cooling, the lower water layer was separated, and the organic layer was washed with water until neutral. Dry over anhydrous sodium sulfate and transfer to a rotary evaporator. The solvent was decompressed by the oil pump, and a loose white irregular powder was obtained in the rotary evaporating bottle, which was poured out and weighed 41g. The liquid chromatography content is 93.21%, based ...

Embodiment 2

[0028] In a 2000ml four-necked flask equipped with an electric stirrer, a thermometer, a reflux condenser, and an oil bath heating pot, add 50g (0.097mol) N-benzoyl-O, O-p-toluenesulfonyl-diethanolamine, 37g (0.1mol) N,N'-di(p-toluenesulfonyl)ethylenediamine, 800ml xylene, 100ml tap water, 66g (0.48mol) anhydrous potassium carbonate, after adding the above materials, start to stir and heat up.

[0029] When the temperature rose to 98°C, the system boiled and there was reflux in the reflux condenser. Timing heat preservation and reflux, after heat preservation for 24 hours, after cooling, the lower water layer was separated, and the organic layer was washed with water until neutral. Dry over anhydrous sodium sulfate and transfer to a rotary evaporator. The oil pump decompresses and spins out the solvent, and loose white irregular powder is obtained in the rotary evaporating bottle, which is poured out and weighed to be 45g. The liquid chromatography content is 96.09%, and the...

Embodiment 3

[0031] In a 2000ml four-necked flask equipped with an electric stirrer, a thermometer, a reflux condenser, and an oil bath heating pot, add 50g (0.097mol) N-benzoyl-O, O-p-toluenesulfonyl-diethanolamine, 37g (0.1mol) N,N'-di(p-toluenesulfonyl)ethylenediamine, 800ml xylene, 100ml tap water, 50g (0.47mol) anhydrous sodium carbonate, after adding the above materials, start to stir and heat up.

[0032] When the temperature rose to 98°C, the system boiled and there was reflux in the reflux condenser. Timing heat preservation and reflux, after heat preservation for 24 hours, after cooling, the lower water layer was separated, and the organic layer was washed with water until neutral. Dry over anhydrous sodium sulfate and transfer to a rotary evaporator. The oil pump decompresses and spins out the solvent, and loose white irregular powder is obtained in the rotary evaporating bottle, which is poured out and weighed to be 33g. The liquid chromatography content is 89.56%, and the mo...

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Abstract

The invention discloses a synthesis method of 1,4-bis(p-toluenesulfonyl)-7-benzoyl trinitrocyclononane, which comprises the following steps of: By taking N-benzoyl-O,O-p-toluenesulfonyl-diethanol amine and N,N'-bis(p-toluenesulfonyl)ethylenediamine as substrates and anhydrous potassium carbonate or anhydrous sodium carbonate as an acid-binding agent, carrying out two-phase reaction in a two-phase solvent of toluene or xylene and water to obtain the 1,4-bis(p-toluenesulfonyl)-7-benzoyl triazacyclononane. The molar ratio of the N-benzoyl-O,O-p-toluenesulfonyl-diethanol amine to the N,N'-di(p-toluenesulfonyl)ethylenediamine is 1:(1-1.05), the molar ratio of the acid-binding agent to the N-benzoyl-O,O-p-toluenesulfonyl-diethanol amine is (3-5):1, the reaction temperature is 90-100 DEG C, and the reaction time is 5-20 hours. The highest reaction yield can reach 85% or above, the reaction product can reach 96% or above without refining, and the synthesis requirements of various organic ligands are completely met. The process provided by the invention improves the intrinsic safety of the technological process, reduces the production and management cost, and has the advantages of mild reaction conditions and low production cost.

Description

technical field [0001] The invention relates to a synthesis method of 1,4-bis(p-toluenesulfonyl)-7-benzoyltriazacyclononane. Background technique [0002] 1,4-bis(p-toluenesulfonyl)-7-benzoyltriazacyclononane, the molecular structure formula is: [0003] [0004] 1,4-bis(p-toluenesulfonyl)-7-benzoyltriazacyclononane is an important organic ligand intermediate. It has two p-toluenesulfonyl groups and one benzoyl group in its molecular structure, and the deprotection conditions of these two protecting groups are completely different, so it can be used to synthesize three N atoms on triazacyclononane Organic ligand compounds with different substituent groups. [0005] At present, the synthetic method of 1,4-bis(p-toluenesulfonyl)-7-benzoyltriazacyclononane is to synthesize 1,4,7-tris(p-toluenesulfonyl)triazacyclononane by traditional method. Nonane, and then remove a p-toluenesulfonyl group under the condition of hydrogen bromide or propionic acid to obtain 1,4-bis(p-tolu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D255/02
CPCC07D255/02
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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