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Synthetic method for 3,7,10-trioxo-2,4,6,8,9,11-hexa aza(3,3,3)propellane

A synthetic method, trioxo technology, applied in the direction of organic chemistry, can solve the problems of complex operation process, many reaction steps, low total yield, etc., and achieve the effect of simple operation process

Active Publication Date: 2016-02-03
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many reaction steps in this method, the total reaction steps are two steps, and the operation process is complex, involving various processes such as extraction, distillation, chromatographic column purification, etc., and the total yield of this method is low, and its total yield is about 80.2%.

Method used

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  • Synthetic method for 3,7,10-trioxo-2,4,6,8,9,11-hexa aza(3,3,3)propellane
  • Synthetic method for 3,7,10-trioxo-2,4,6,8,9,11-hexa aza(3,3,3)propellane
  • Synthetic method for 3,7,10-trioxo-2,4,6,8,9,11-hexa aza(3,3,3)propellane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 35.1mmol diaminoglycoluril and 40.36mmol N,N'-carbonyldiimidazole to 120ml dimethyl sulfoxide under stirring at a temperature of 20°C. After the addition, react for 60 hours, pour the reaction solution into acetone, and filter , the filter cake was washed with methanol, and dried to obtain 5.95 g of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3,3,3]propeller, yield 85.6 %.

[0018] Structure Identification:

[0019] Infrared spectrum: IR (KBr) ν: 3218, 2830, 1747, 1688, 1524, 1471cm -1 ;

[0020] NMR spectrum: 1 HNMR (DMSO-d 6 ,500MHz), δ: 8.06(s,6H);

[0021] 13 CNMR (DMSO-d 6 ,125MHz), δ: 159.4,85.2;

[0022] MS:199(M+)

[0023] Elemental analysis: Molecular formula: C 5 h 6 N 6 o 3

[0024] Theoretical value: C30.31, H3.05, N42.41

[0025] Measured values: C29.94, H3.42, N41.98.

[0026] The above structural identification data confirm that the substance obtained in this step is indeed 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3,3,3]propellerane.

Embodiment 2

[0028] Add 35.1mmol diaminoglycoluril and 36.86mmol N,N'-carbonyldiimidazole to 108ml dimethyl sulfoxide under stirring at a temperature of 20°C. After the addition, react for 70 hours, pour the reaction solution into acetone, and filter , the filter cake was washed with methanol and dried to obtain 5.93 g of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3,3,3]propeller, yield 85.3 %.

Embodiment 3

[0030] Under stirring, at a temperature of 15°C, add 35.1mmol diaminoglycoluril and 36.86mmol N,N'-carbonyldiimidazole to 150ml dimethyl sulfoxide respectively. After the addition, react for 50 hours, pour the reaction solution into acetone, and filter , the filter cake was washed with methanol, and dried to obtain 5.91 g of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3,3,3]propeller, yield 85.1 %.

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Abstract

The invention discloses a synthetic method for 3,7,10-trioxo-2,4,6,8,9,11-hexa aza(3,3,3)propellane. The method comprises the following steps that at the temperature of 15 DEG C-30 DEG C, diamino glycoluril and N,N'-carbonyldiimidazole are added into dimethyl sulfoxide in a stirred mode, after feeding is finished, the reaction is carried out for 50-80 h, then reaction liquid is poured into acetone and filtered, filter cake is washed with methyl alcohol and dried to obtain 3,7,10-tri oxo-2,4,6,8,9,11-hexa aza(3,3,3)propellane, the molar ratio of diamino glycoluril to N,N'-carbonyldiimidazole is 1:1.05-1.3, and the mass ratio of diamino glycoluril to N,N'-carbonyldiimidazole is 1:18-25.

Description

technical field [0001] The invention relates to a synthesis method of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3,3,3]propeller, belonging to the field of energetic materials. Background technique [0002] Propellane is a special fused tricyclic ring system, which is the basic skeleton structure of many products and has important biological and pharmacological activities. In the past 30 years, it has attracted the attention of many chemists because of its unique structure. interest. In recent years, energetic materials researchers have applied propane structures to the design and synthesis of energetic materials. Compared with traditional CHON component materials, such as TNT, RDX and HMX, propane energetic compounds not only have With high enthalpy of formation and high energy density, it is a class of energetic materials that are expected to break through the energy threshold of CHON materials. Among them, 2,4,6,8,9,11-hexanitro-2,4,6,8,9,11-hexaaza[3,3,3]propeller with excelle...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/18
CPCC07D487/18
Inventor 毕福强王锡杰王伯周汪伟廉鹏张俊林霍欢
Owner XIAN MODERN CHEM RES INST
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