Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of synthetic method of nitroazole energetic compound

A synthesis method and compound technology, applied in the field of synthesis of nitrogen nitration products, can solve problems such as the lack of overall reaction mechanism, and achieve the effects of simple reaction process, high yield, and good substrate universality

Active Publication Date: 2020-10-30
NANJING UNIV OF SCI & TECH
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, further theoretical studies and experimental verification of its subsequent intermediates or reaction processes have not been reported, so the overall reaction mechanism still lacks strong support

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of nitroazole energetic compound
  • A kind of synthetic method of nitroazole energetic compound
  • A kind of synthetic method of nitroazole energetic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of N-nitropyrazole

[0031]

[0032] In an oven-dried three-necked flask (25mL) equipped with a stirring bar, add pyrazole (1.0mmol, 68mg), electrolyte n-Bu 4 NBF 4 (205mg, 0.6mmol) and ferric nitrate nonahydrate (2.0mmol, 0.808g). The three-necked flask is equipped with a graphite rod (Φ=6mm) as the anode, and a platinum plate electrode (10mm×10mm) as the cathode, and 16mL of CH 3 CN, then evacuated and flushed with nitrogen as a protective gas. The reaction mixture was stirred at reflux for 6 hours at a constant current of 15 mA at 70°C. When the reaction was completed, the reaction mixture was washed with water twice and extracted with ethyl acetate (10 mL×3). Then the organic layers were combined and washed with Na 2 SO 4 Concentrate in vacuo after drying, then obtain pure product by flash chromatography column, be white powdery solid, productive rate is 64%, the NMR characteristic of this product is: 1 H NMR (500MHz, Chloroform-d) δ = 8.36 (d, J...

Embodiment 2

[0034] Synthesis of N-nitropyrazole

[0035]

[0036] The reaction steps are exactly the same as in Example 1, except that tetrabutyl ammonium tetrafluoroborate is changed into tetrabutyl ammonium perchlorate, and the product is a white powdery solid with a yield of 53%. The NMR of this product is characterized by : 1 H NMR (500MHz, Chloroform-d) δ = 8.36 (d, J = 2.8, 1H), 7.66 (s, 1H), 6.55–6.48 (m, 1H). 13 C NMR (126MHz, Chloroform-d) δ=140.98, 125.24, 109.36.

Embodiment 3

[0038] Synthesis of N-nitropyrazole

[0039]

[0040] The reaction steps are exactly the same as in Example 1, except that ferric nitrate nonahydrate is changed to bismuth nitrate pentahydrate, and the product is a white powdery solid with a yield of 43%. The NMR characterization of this product is: 1 H NMR (500MHz, Chloroform-d) δ = 8.36 (d, J = 2.8, 1H), 7.66 (s, 1H), 6.55–6.48 (m, 1H). 13 C NMR (126MHz, Chloroform-d) δ=140.98, 125.24, 109.36.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing N-nitrated compounds of azoles. Through an electrocatalytic free radical coupling reaction, economical and non-toxic metal nitrate is used as a nitro source to carry out N-H bonds of azoles. No oxidation and nitrification reaction. The present invention adopts the mode of electrocatalysis, adopts various cheap metal nitrates as nitrate sources, and adopts a one-step method to synthesize the target product. High, and realize a green N‑N single bond construction method.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry and relates to a synthesis method of nitrogen nitration products of azoles. Background technique [0002] Formation of N-NO by N-nitration 2 is one of the most common methods to obtain N-N bonds by functionalizing N-H groups. The product N-nitroamine is a substance that widely exists in azo dyes and high-density energetic materials. The common energetic compounds hexanitrohexaazaisowurtzitane (CL-20), 1,3,5,7-tetra Nitro-1,3,5,7-tetraazacycloctane (HMX) has N-NO 2 Therefore, finding effective strategies to efficiently construct N–N bonds to prepare N-nitro compounds has become an important research topic in synthetic chemistry. [0003] The conventional mechanism of N-nitration involves 3 ) from NO 3 - In situ generation of nitronium ions (NO 2 + ). then NO 2 + A two-electron transfer addition (polar addition, Ingold-Hughes method) or one-electron transfer (SET, Kenner-Weiss m...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 王鹏程赵季平陆明周新利
Owner NANJING UNIV OF SCI & TECH