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Synthesis method of trinitrobenzo [4, 5] imidazo [2, 1-c] [1, 2, 4] triazine-4-one

A technology of aminobenzimidazole and trinitrobenzene, which is applied in organic chemistry and other fields, can solve the problems of limited energetic group modification sites and small conjugated systems, and achieves easy-to-obtain, reproducible, and cheap Effect

Active Publication Date: 2020-08-14
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many classic simple explosive molecules including TNT, PTX, etc. have been synthesized and reported one after another, most of the reported ones are monocyclic or bicyclic structures, with limited modification sites of energetic groups and relatively small conjugated systems, which urgently need to be synthesized. Larger energetic conjugated frameworks for the design and development of energetic molecules

Method used

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  • Synthesis method of trinitrobenzo [4, 5] imidazo [2, 1-c] [1, 2, 4] triazine-4-one
  • Synthesis method of trinitrobenzo [4, 5] imidazo [2, 1-c] [1, 2, 4] triazine-4-one
  • Synthesis method of trinitrobenzo [4, 5] imidazo [2, 1-c] [1, 2, 4] triazine-4-one

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 0.4 g (3.0 mmol) of 2-aminobendazole was mixed with 3 ml of distilled water to form a suspension. At 0°C, 0.9 ml of 38% concentrated hydrochloric acid (12M) was added dropwise to the reaction system. At the same temperature, 0.24 g of sodium nitrite solution (3.5 mmol) dissolved in 1.5 ml of distilled water was added dropwise, and stirring was continued for 0.5 h. At the same time, 0.12 g of sodium hydroxide (3 mmol) was dissolved in 20 ml of distilled water, and 0.26 g of nitroacetonitrile (3 mmol) was added dropwise in an ice bath environment to prepare the sodium salt of nitroacetonitrile. The sodium salt solution was added dropwise to the above reaction system, and stirred for 3 days after naturally rising to room temperature. The reaction solution was extracted with ethyl acetate, and the combined organic phase was dried over anhydrous sodium sulfate, concentrated by rotary evaporation, and separated by column chromatography to obtain 242 mg of the target product ...

Embodiment 2

[0029] 0.4 g (3.0 mmol) of 2-aminobendazole was mixed with 3 ml of distilled water to form a suspension. At 0°C, 0.9 ml of 38% concentrated hydrochloric acid (12M) was added dropwise to the reaction system. At the same temperature, 0.24 g of sodium nitrite solution (3.5 mmol) dissolved in 1.5 ml of distilled water was added dropwise, and stirring was continued for 0.5 h. At the same time, 0.24 g of sodium hydroxide (6 mmol) was dissolved in 20 ml of distilled water, and 0.52 g of nitroacetonitrile (6 mmol) was added dropwise in an ice bath environment to prepare the sodium salt of nitroacetonitrile. The sodium salt solution was added dropwise to the above reaction system, and stirred for 3 days after naturally rising to room temperature. The reaction solution was extracted with ethyl acetate, and the combined organic phase was dried over anhydrous sodium sulfate, concentrated by rotary evaporation, and separated by column chromatography to obtain 193 mg of the target product ...

Embodiment 3

[0031] 0.4 g (3.0 mmol) of 2-aminobendazole was mixed with 15 ml of distilled water to form a suspension. At 0°C, 0.9 ml of 38% concentrated hydrochloric acid (12M) was added dropwise to the reaction system. At the same temperature, 0.24 g of sodium nitrite solution (3.5 mmol) dissolved in 1.5 ml of distilled water was added dropwise, and stirring was continued for 0.5 h. At the same time, 0.24 g of sodium hydroxide (6 mmol) was dissolved in 20 ml of distilled water, and 0.52 g of nitroacetonitrile (6 mmol) was added dropwise in an ice bath environment to prepare the sodium salt of nitroacetonitrile. The sodium salt solution was added dropwise to the above reaction system, and stirred for 3 days after naturally rising to room temperature. The reaction solution was extracted with ethyl acetate, and the combined organic phase was dried over anhydrous sodium sulfate, concentrated by rotary evaporation, and separated by column chromatography to obtain 124 mg of the target product...

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Abstract

The invention discloses a synthesis method of trinitrobenzo [4, 5] imidazo [2, 1-c] [1, 2, 4] triazine-4-one, and the method comprises the following steps: adding concentrated sulfuric acid into a reaction flask at low temperature, adding 3-nitro-4-amino-benzo [4, 5] imidazo [2, 1-c] [1, 2, 4] triazine in batches, and stirring; dropwise adding fuming nitric acid, heating to obtain a first reactionsystem after the reaction is finished, pouring the first reaction system into ice water, extracting a water phase by using ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, concentrating the organic phases to obtain a crude product, and further purifying the crude product through column chromatography to obtain 3, 7, 9-trinitrobenzo [4, 5] imidazo [2, 1-C] [1, 2, 4] triazine-4 (3H)-one and 3, 9-dinitrobenzo [4, 5] imidazo [2, 1-C] [1, 2, 4] triazine-4 (3H)-one. The raw material 2-aminobenzimidazole used in the reaction is a commercialized product in the market, and is low in price and easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of energetic materials, and in particular relates to a synthesis method of trinitrobenzo[4,5]imidazo[2,1-c][1,2,4]triazin-4-one. Background technique [0002] Modern warfare not only requires weapons and equipment to have strong damage capabilities, but also puts forward higher requirements for the safety performance of energetic materials. In recent years, scientists have explored the skeleton structure of insensitive high-energy compounds through various methods such as calculation and synthesis to obtain new energetic materials with better mechanical properties and stability. Due to the large conjugated system and stable aromatic structure, conjugated ring energetic molecules usually have very good thermal stability and low friction and impact sensitivity. By increasing the number of conjugated rings and the functional group modification sites on the backbone, the structural stability and mechanical sens...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 杨炜贾云飞黄靖伦范桂娟
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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