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Preparation method of 3-aminofurazan-4-methanamide

A technology of aminofurazan and formamide, which is applied in the field of organic intermediate synthesis, can solve the problems of poor reaction selectivity, low yield, cumbersome synthesis steps, etc., and achieve easy-to-obtain raw materials, high purity and yield, and simple process flow Effect

Active Publication Date: 2018-09-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In order to solve the above problems such as low product yield, poor reaction selectivity, and complicated synthesis steps, the invention provides a method for preparing 3-aminofurazan-4-carboxamide using cyanoacetamide as a raw material. The raw material of the method is simple and easy to obtain , the post-treatment is simple and the yield is high, which solves the problem that 3-aminofurazan-4-carboxamide is difficult to prepare from simple raw materials, and is a new green synthesis method

Method used

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  • Preparation method of 3-aminofurazan-4-methanamide

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Experimental program
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Effect test

Embodiment 1

[0031] The first step: the synthesis of 2-oximino cyanoacetamide (2)

[0032]

[0033] Add 100mL of deionized water into a 250mL reaction flask, then weigh cyanoacetamide 1 (12.61g, 0.15mol) and sodium nitrite (12.42g, 0.18mol) into the reaction flask in turn, add ice Acetic acid (17.1 mL, 0.3 mol) was dropped, stirred at room temperature for 10 h, and the reaction progress was tracked by TLC. After the reaction was completed, a white filter cake was obtained by suction filtration, and dried in an oven to obtain a white powder (14.48 g, molar yield 85.4%).

[0034] Melting point: 171.8°C-172.0°C

[0035] 1 H NMR (500MHz, DMSO-d 6 )δ: 7.83, 7.91 (2br s, 2H, CON H 2 ),14.48(s,1H,O H ).

[0036] The second and third one-pot synthesis: Synthesis of 3-aminofurazan-4-carboxamide (4)

[0037]

[0038] Add 3.6mL of anhydrous methanol in the dry reaction flask, weigh the methanol solution (1.47g, 7.5mmol) of sodium methoxide (1.47g, 7.5mmol) and hydroxylamine hydrochloride ...

Embodiment 2

[0040] The first step: the synthesis of 2-oximino cyanoacetamide (2)

[0041] Add 63mL of deionized water into a 250mL reaction flask, then weigh cyanoacetamide 1 (12.61g, 0.15mol) and sodium nitrite (11.38g, 0.16mol) into the reaction flask in turn, add formic acid dropwise under ice-water bath conditions (8.5mL, 0.22mol), after dropping, stir at room temperature for 8h, and track the reaction progress by TLC. After the reaction was completed, a white filter cake was obtained by suction filtration, and dried in an oven to obtain a white powder (14.07 g, molar yield 83.0%).

[0042] The second and third one-pot synthesis: Synthesis of 3-aminofurazan-4-carboxamide (4)

[0043] Add 4.6mL of anhydrous methanol to the dry reaction flask, weigh the ethanol solution (3.20g, 10mmol) of sodium ethoxide (3.20g, 10mmol) and hydroxylamine hydrochloride (0.70g, 10mmol) with a mass fraction of 21% and drop into the reaction flask in turn, and stir for 0.5h . Then add 2 (0.57g, 5mmol), a...

Embodiment 3

[0045] The first step: the synthesis of 2-oximino cyanoacetamide (2)

[0046] Add 113mL of deionized water into a 250mL reaction flask, then weigh cyanoacetamide 1 (12.61g, 0.15mol) and sodium nitrite (10.35g, 0.15mol) into the reaction flask in turn, add the mass of Sulfuric acid (11.9 mL, 0.15 mol) with a fraction of 75% was added dropwise, stirred at room temperature for 12 h, and the reaction progress was tracked by TLC. After the reaction was completed, a white filter cake was obtained by suction filtration, and dried in an oven to obtain a white powder (13.92 g, molar yield 82.1%).

[0047] The second and third one-pot synthesis: Synthesis of 3-aminofurazan-4-carboxamide (4)

[0048] Add 11mL of anhydrous tert-butanol to the dry reaction flask, weigh sodium tert-butoxide (0.48g, 5mmol) and hydroxylamine hydrochloride (0.35g, 5mmol) into the reaction flask in turn, and stir for 0.5h. Then add 2 (0.57g, 5mmol), and stir at 85°C for 5h. After the reaction is completed, th...

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Abstract

The invention discloses a preparation method of 3-aminofurazan-4-methanamide. The method comprises the following steps: cyanoacetamide is subjected to nitrosation and isomerization to prepare 2-oximido cyanoacetamide, 2-oximido cyanoacetamide and hydroxylamine hydrochloride and organic base are subjected to a reaction to prepare an amidoxime intermediate which is 2-oximido-3-amidoxime acetamide, and the 2-oximido-3-amidoxime acetamide is subjected to a closed loop reaction under effect of thionyl chloride to generate a target product 3-aminofurazan-4-methanamide. The method has the advantagesof simple process flow, easily available raw material, and high product yield, and is suitable for industrial product, and is the novel synthetic method for 3-aminofurazan-4-methanamide.

Description

technical field [0001] The invention belongs to the preparation of energetic materials in the technical field of organic intermediate synthesis, and in particular relates to a preparation method of 3-aminofurazan-4-carboxamide. Background technique [0002] Furazan ring is a five-membered ring containing two nitrogen atoms and one oxygen atom, also known as 1,2,5-oxadiazole ring (1,2,5-oxadiazole). This kind of compound is a very effective energy-containing structural unit due to its high formation enthalpy, good thermal stability, active oxygen in the ring, and aromatic large π-conjugated system in the molecule. Studies have shown that the furazan ring in the molecule can greatly increase the energy of the molecule, and it will be released under specific conditions, so it has attracted extensive attention from scholars at home and abroad. [0003] 3-Aminofurazan-4-carboxamide is a simple furazan compound, which reacts with different reagents by utilizing the activity of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/08
CPCC07D271/08
Inventor 戴立言李俊张玲玲王晓钟陈英奇
Owner ZHEJIANG UNIV
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