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Azo-furazan compound and preparing method thereof

An azofurazan and compound technology, which is applied in the field of azofurazan compounds and their preparation, can solve the problems of few and single azofurazan compounds, and achieves the effects of simple preparation, high safety and low cost

Active Publication Date: 2016-03-23
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

But the synthetic method report of azofurazan compound is few at present (J.Org.Chem.1996,61,1510-1511; Russian Chemical Bulletin, International Edition, 54,8,1915-1922,2005; 2010; PropellantsExplos.Pyrotech.2011,36,233–239; J.Phys.Chem.C, 2015,119,12887-12895), only a single azofurazan compound can be obtained
At present, there are few reports at home and abroad on the preparation methods of low-cost, high-throughput synthesis of azofurazan compounds and their derivatives

Method used

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  • Azo-furazan compound and preparing method thereof
  • Azo-furazan compound and preparing method thereof
  • Azo-furazan compound and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of 4-aminofurazan-3-amidoxime (AFA)

[0033]

[0034] Preheat 70mL of water to 45°C, add malononitrile (3.20g, 50mmol), and stir at this temperature for 5min. Cool in an ice bath to 0°C-5°C, and add sodium nitrite (3.80 g, 55 mmol). At this temperature, 6 mol / L hydrochloric acid (0.55 mL) was added, and the temperature was gradually raised to 10°C. After 15 minutes, the ice bath was removed, and the stirring reaction was continued for 1.5 hours. Then the reaction system was cooled to about 10°C, and 50% aqueous hydroxylamine solution (9.90 g, 150 mmol) was added in one go. The reaction temperature was gradually raised to 25 °C, and the reaction was continued at this temperature for 1 h. Further reflux reaction for 2h, naturally cooled to room temperature. Under cooling in an ice bath, the temperature of the system was controlled below 5 °C, and the pH was adjusted to 7.0 with 6 mol / L hydrochloric acid (8.0 mL). Filtration, the resulting precipitate was ...

Embodiment 2

[0041] Preparation of 4-amino-3-cyanofurazan

[0042]

[0043] 1.14g (8mmol) of AFA was dissolved in 5ml of acetic acid at 20°C, and 1.78g (7.4mmol) of lead dioxide was added. Stir at room temperature for 5 h, filter, extract with ethyl acetate, neutralize with saturated sodium carbonate solution, dry over anhydrous sodium sulfate, evaporate ethyl acetate to dryness under reduced pressure, add the solid into dichloromethane and stir for 30-60 min, Filtration followed by removal of dichloromethane gave 4-amino-3-cyanofrazan.

[0044] Melting point: 85-87°C.

[0045] Mass spectrum: 110 (M+).

[0046] 1H-NMR: 7.11 (s, 1H).

[0047] 13C-NMR: 157.45; 126.47; 108.69.

[0048] Or dissolve 8mmol AFA in 5ml acetic acid at 25°C, add 8mmol lead dioxide and stir at room temperature for 1h, filter, extract with ethyl acetate, neutralize with saturated sodium carbonate solution, dry over anhydrous sodium sulfate, and reduce pressure The ethyl acetate was evaporated to dryness, the s...

Embodiment 3

[0050] Preparation of 3-amino-4-(1,2,3,4-tetrazol-5-yl)furazan

[0051]

[0052] Using the same method as in Example 2, 4-amino-3-cyanofurazan was obtained, and then reacted with hydrazine hydrate at a temperature of 15° C. for 10 h according to a molar ratio of 1:8 to obtain a white solid (4-amino-1,2,5 -oxazole-3-acylhydrazone), white solid and sodium nitrite were reacted for 10h in 20% hydrochloric acid at a molar ratio of 1:2 at a temperature of 35°C to obtain 3-amino-4-(1,2 ,3,4-tetrazol-5-yl)furazan.

[0053] Mass spectrum: 151.8 (M-).

[0054] Or adopt the same method as in Example 2 to obtain 4-amino-3-cyanofurazan, then react with hydrazine hydrate at a temperature of 30° C. for 5 h to obtain a white solid according to a molar ratio of 1:10, and mix the white solid with sodium nitrite in The temperature was 15°C and the reaction was carried out in 15% hydrochloric acid with sufficient concentration for 15 hours according to the molar ratio of 1:5 to obtain 3-amin...

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Abstract

The invention discloses an azo-furazan compound and a preparing method thereof. The preparing method includes the specific steps that malononitrile serves as a raw material and is reacted with an oxidizing agent to obtain an amino-oximido furazan intermediate; the amino-oximido furazan intermediate is reacted with different cyclization reagents (triethyl orthoformate, bromized nitrile, acetic anhydride, trifluoroacetic anhydride and the like) to obtain an amidogen-substituted furazan intermediate, then the furazan intermediate is reacted with potassium permanganate and hydrochloric acid of 10%-20%, and the azo-furazan compound is separated and precipitated. The preparing method is simple; compared with the prior art, azo-furazan compounds with different substituent groups can be prepared at a time in a high throughput mode, operation is safe, and cost is low.

Description

technical field [0001] Embodiments of the present invention relate to the preparation of energetic materials in the field of organic synthesis, and more specifically, embodiments of the present invention relate to azofurazan compounds and preparation methods thereof. Background technique [0002] Among the high-nitrogen energetic compounds, the most studied and typical ones are azole energetic compounds. Especially energetic derivatives with furazan ring (1,2,5-oxadiazole) and triazole ring as basic structural units, by introducing energetic side groups to it, such as nitro, triazole ring, tetrazole ring , azido, etc., can obtain a series of nitrogen-rich and high-energy energy-containing compounds of furazans. Furazan has an aromatic-like large π-conjugated system, which improves the stability and energy density of the compound; the oxygen atom on the furazan ring is not directly connected to a carbon or hydrogen atom, and is an effective oxygen, which is combined with car...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/08C07D413/14
CPCC07D271/08C07D413/14
Inventor 屈延阳李海波李洪珍赵银巧杨光成
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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