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Nitryl or dinitrophenyl-benzo[1,2,3] triazole, derivative and preparation methods

A kind of technology of dinitrophenyl, triazole derivatives

Active Publication Date: 2017-06-20
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no report about benzotriazole and nitrobenzene structural coupling structure and preparation method (Chemical Intermediates, 2011, 05, 14-16; Shandong Chemical Industry, 2012, 41, 54-56; Eur.J .Inorg.Chem.2016,956–962; J.Heterocyclic Chem.,52,1314(2015);)

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  • Nitryl or dinitrophenyl-benzo[1,2,3] triazole, derivative and preparation methods
  • Nitryl or dinitrophenyl-benzo[1,2,3] triazole, derivative and preparation methods
  • Nitryl or dinitrophenyl-benzo[1,2,3] triazole, derivative and preparation methods

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Embodiment 1

[0040] The preparation of embodiment 1 compound 1:

[0041]

[0042] Add 0.2mol (23.826g) benzotriazole, and 0.2mol (40.39g) 1-chloro-2,4-dinitrobenzene into a 500ml s flask, add 300ml organic solvent, 0.2mol solid base, and heat to 80 degrees (internal temperature) can be reacted for 16 or 24 hours. Prohibition of cooling, a part of the product (about 50%, 28g) will be precipitated, and the precipitation point is very pure (product). The remaining liquid can be added to the organic solvent to rinse the spin-dried product, or it can be directly passed through the column. A total of 47.9 g of the product was obtained. Yield 84%.

[0043] Mass spectrum of target product: ESI M + = 285.0556.

[0044] 1H-NMR: 9.10(d, J=6.0Hz, 1H); 8.84(q, J=12.0Hz, 1H); 8.43(d, J=12.0Hz, 1H); 8.29(d, J=12.0Hz, 1H ); 7.88 (d, J = 12.0 Hz, 1H); 7.78 (m, 1H); 7.62 (m, 1H).

[0045] 13C-NMR: 147.83; 145.81; 144.54; 133.06; 132.87; 130.34; 129.69; 129.35; 126.05;

Embodiment 2

[0046] The preparation of embodiment 2 compound 2:

[0047]

[0048] Add 0.4mol (47.65g) benzotriazole, and 0.2mol (49.39g) 1-chloro-2,4,6-trinitrobenzene into a 500ml s flask, add 300ml organic solvent, 0.2mol solid base, Heated to 80 degrees (internal temperature) for 16 or 24 hours to react. Direct organic reagents through the column. The product Compound 2 was obtained: 44.0 g, yield 54.6%.

[0049] Mass spectrum of target product: ESI M - = 401.0753.

[0050] 13C-NMR: 148.92; 148.69; 146.73; 145.41; 145.20; 134.15; 130.78; 129.38; 126.25;

Embodiment 3

[0051] The preparation of embodiment 3 compound 3:

[0052]

[0053] Add 0.4mol (47.65g) benzotriazole, and 0.2mol (49.39g) 1-chloro-2,4,6-trinitrobenzene into a 500ml s flask, add 300ml organic solvent, 0.2mol solid base, Heated to 80 degrees (internal temperature) for 16 or 24 hours to react. Direct organic reagents through the column. The product compound 3 was obtained: 26.42g, the yield was 33%.

[0054] Mass spectrum of the target product: ESI[M+Na+K]=466.8278.

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Abstract

The invention discloses structures of nitrophenyl-benzo[1,2,3] triazole, dinitrophenyl-benzo[1,2,3] triazole and a dinitrophenyl-benzo[1,2,3] triazole derivative, and mass spectrometry information thereof. In addition, the invention also discloses preparation methods for the nitrophenyl-benzo[1,2,3] triazole, the dinitrophenyl-benzo[1,2,3] triazole and the dinitrophenyl-benzo[1,2,3] triazole derivative. According to the preparation methods, novel compound structures of the nitrophenyl-benzo[1,2,3] triazole and the dinitrophenyl-benzo[1,2,3] triazole derivative are prepared, which can be applied to novel materials for the fields, such as energetic materials, oil exploitation and space exploration. Synthesis methods provided by the invention have the characteristics that raw materials are easy to obtain, the operation is simple and convenient, the safety is high, the process is controllable and the like.

Description

technical field [0001] The present invention relates to energetic materials and preparation methods thereof, in particular to nitrophenyl-benzo[1,2,3]triazole, dinitrophenyl-benzo[1,2,3]triazole, and dinitrophenyl-benzo[1,2,3]triazole A nitrophenyl-benzo[1,2,3]triazole derivative and a preparation method thereof belong to the field of organic synthesis. Background technique [0002] The earliest research on heat-resistant explosives was mainly to meet military needs, such as space vehicles, spaceships, and spaceships that are subjected to high-temperature environments. At present, its main application is perforating and blasting equipment for oil and gas wells. With the development of fields such as space programs and deep oil drilling, the need for heat-resistant or thermally stable explosives is more urgent. The production of safe and reliable explosives or mixed explosives at high temperatures has become a research hotspot that is actively pursued all over the world. A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/18C07D249/20C07D401/04
CPCC07D249/18C07D249/20C07D401/04
Inventor 屈延阳聂福德赵银巧黄靖伦范桂娟
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS