Synthesis method of 5,5'-di(acetic ether)-3,3'-bi-1,2,4-oxadiazole

An ethyl acetate-based, synthetic method technology, applied in organic chemistry and other directions, can solve problems such as poor selectivity and low yield, and achieve the effects of improving selectivity and reducing reaction temperature

Active Publication Date: 2017-05-10
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The selectivity of this synthetic method is poor, and the target compound needs to be separated by column chromatography, and the yield is low, only 23%.

Method used

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  • Synthesis method of 5,5'-di(acetic ether)-3,3'-bi-1,2,4-oxadiazole
  • Synthesis method of 5,5'-di(acetic ether)-3,3'-bi-1,2,4-oxadiazole
  • Synthesis method of 5,5'-di(acetic ether)-3,3'-bi-1,2,4-oxadiazole

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Experimental program
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Effect test

Embodiment 1

[0021] Example 1 Synthesis of 5,5'-diacetoxyethyl-3,3'-bi-1,2,4-oxadiazole

[0022] (1) Under the condition of 25°C, add 30ml of ethylene glycol dimethyl ether and 1.6g of pyridine into the reaction flask in turn, after stirring evenly, add 1.2g of diaminoglyoxime in batches, stir until completely dissolved, drop Add 3.0 g of ethyl chloroformoacetate, and react at 40°C for 30 min;

[0023] (2) Continue to heat the reaction solution obtained in step (1) to 100°C, and after continuing to react for 2 hours, pour the reaction solution into water, extract with chloroform, dry and distill under reduced pressure to obtain ethyl 5,5′-diacetate Base-3,3'-bi-1,2,4-oxadiazole was 1.92 g, and the yield was 62%.

[0024] Structure Identification:

[0025] Elemental analysis:

[0026] Molecular formula: C 12 h 14 N 4 o 6

[0027] Theoretical value: C 46.45, H 4.55, N 18.06;

[0028] Found: C 46.51, H 4.52, N 18.10.

[0029] Infrared (KBr, cm -1 ): 3473, 3376, 3180, 2976, 1751, 16...

Embodiment 2

[0034] (1) Under the condition of 25°C, add 25ml of ethylene glycol dimethyl ether and 0.4g of pyridine into the reaction flask in turn, after stirring evenly, add 1.2g of diaminoglyoxime in batches, stir until completely dissolved, drop Add 1.5 g of ethyl chloroformoacetate, and react at 30°C for 40 minutes;

[0035] (2) Continue to heat the reaction solution obtained in step (1) to 80°C, and after continuing the reaction for 3 hours, pour the reaction solution into water, extract with chloroform, dry and distill under reduced pressure to obtain ethyl 5,5′-diacetate Base-3,3'-bi-1,2,4-oxadiazole 1.86g, yield 60%.

Embodiment 3

[0037] (1) Under the condition of 25°C, add 40ml of ethylene glycol dimethyl ether and 2.0g of pyridine into the reaction flask in turn, after stirring evenly, add 1.2g of diaminoglyoxime in batches, stir until completely dissolved, drop Add 4.5 g of ethyl chloroformoacetate, and react at 40°C for 20 min;

[0038] (2) Continue to heat the reaction solution obtained in step (1) to 100°C, and after continuing to react for 2 hours, pour the reaction solution into water, extract with chloroform, dry and distill under reduced pressure to obtain ethyl 5,5′-diacetate Base-3,3'-bi-1,2,4-oxadiazole was 1.92 g, and the yield was 62%.

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Abstract

The invention discloses a synthesis method of 5,5'-di(acetic ether)-3,3'-bi-1,2,4-oxadiazole. The structural formula of the 5,5'-di(acetic ether)-3,3'-bi-1,2,4-oxadiazole is disclosed in the specification. By using diamidoglyoxime and ethyl chloroformylacetate as raw materials, the method comprises the following steps: (1) sequentially adding glycol dimethyl ether and pyridine into a reaction bulb, stirring uniformly, adding the diamidoglyoxime in batches, stirring until the solid is completely dissolved, dropwisely adding the ethyl chloroformylacetate, and carrying out reaction at 30-50 DEG C for 20-40 minutes; (2) heating the reaction solution obtained in the step (1) to 80-120 DEG C, continuing the reaction for 1-3 hours, pouring the reaction solution into water, and carrying out chloroform extraction, drying, reduced pressure distillation and the like to obtain the 5,5'-di(acetic ether)-3,3'-bi-1,2,4-oxadiazole. The synthesis method disclosed by the invention is easy to operate, and has higher reaction yield. The method is mainly used for synthesizing 5,5'-di(acetic ether)-3,3'-bi-1,2,4-oxadiazole.

Description

technical field [0001] The present invention relates to a method for synthesizing bi-1,2,4-oxadiazole derivatives, in particular to a 5,5'-diacetoxyethyl-3,3'-bi-1,2,4 -The synthetic method of oxadiazole. Background technique [0002] 5,5'-diacetoxyethyl-3,3'-bi-1,2,4-oxadiazole is a synthetic 5,5'-dinitroformyl-3,3'-bi-1,2, 4-Oxadiazole, 5,5′-Dinitromethyl-3,3′-bi-1,2,4-oxadiazole and 5,5′-Dinitrofluoromethyl-3, Key intermediates of energetic compounds such as 3'-bi-1,2,4-oxadiazole. "Synthesis of C-Azolylacetic acidesters based on carbethoxyethylacetimidate" (Russian chemical bulletin, 1990,39(9):1888-1895) disclosed a 5,5'-diacetoxyethyl-3,3'-linked-1 , The synthetic method of 2,4-oxadiazole. "5,5′-Bis-(trinitromethyl)-3,3′-bi-(1,2,4-oxadiazole): a stable ternary CNO-compound with high density" followed this synthesis method. Its synthetic steps are as follows: [0003] (1) At room temperature, add 0.017 mol of diaminoglyoxime and 0.063 mol of diethyl malonate to th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/06
CPCC07D271/06
Inventor 黄晓川郭涛王子俊刘敏邱少君姚冰洁李洪丽姜俊唐望吕英迪张彦陈志强石强郑晓东
Owner XIAN MODERN CHEM RES INST
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