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Synthesis method of 1, 2, 4-oxadiazole-3, 5-diketone

A synthesis method and technology for oxadiazole, applied in 1 field, can solve the problems of high cost, complex production conditions and high equipment requirements, and achieve the effects of low production cost, fast reaction rate and low equipment requirements

Pending Publication Date: 2021-08-17
HANGZHOU KAIMING PANGDE BIOTECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The purpose of the present invention is to provide a simple process, suitable reaction conditions, low production cost, fast reaction rate and high yield in order to solve the defects of existing synthetic oxadiazole diones, complex production conditions, high equipment requirements and high cost. Synthetic method of 1,2,4-oxadiazole-3,5-dione

Method used

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  • Synthesis method of 1, 2, 4-oxadiazole-3, 5-diketone
  • Synthesis method of 1, 2, 4-oxadiazole-3, 5-diketone

Examples

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Embodiment 1

[0038] This embodiment provides a synthetic method of 1,2,4-oxadiazole-3,5-dione, comprising the following steps:

[0039] 1) Add compound 1 (10.3g, 0.1mol) and 170mL 1mol / L sodium hydroxide or potassium hydroxide aqueous solution into the flask under ice-water bath conditions. After the addition is complete, slowly add 30% hydrogen peroxide (15.9g) dropwise for 1h After the left and right additions are completed, react at 0°C for 45 minutes, adjust the pH to 4.5 with hydrochloric acid, a white precipitate appears, filter, and recrystallize the filter cake with pure water to obtain compound 2 with a yield of 87%;

[0040] 2) Add compound 2 (10.1g, 0.1mol), 90mL deionized water, and 40g acetic acid into the flask under ice-water bath conditions. After the addition is complete, slowly add 9.7g (0.14mol) of sodium nitrite. After the addition is complete, TLC monitors Reaction, the reaction temperature is 0-5°C, and the reaction time is 8h. After the reaction is completed, the rea...

Embodiment 2

[0042] This embodiment provides a synthetic method of 1,2,4-oxadiazole-3,5-dione, comprising the following steps:

[0043] 1) Add compound 1 (10.3 g, 0.1 mol) and 150 mL of 1 mol / L sodium hydroxide or potassium hydroxide aqueous solution into the flask under ice-water bath conditions. After the addition is complete, slowly add 30% hydrogen peroxide (13.6 g) dropwise for 1 h After the left and right additions are completed, react at 0°C for 45 minutes, adjust the pH to 4.5 with hydrochloric acid, a white precipitate appears, filter, and recrystallize the filter cake with pure water to obtain compound 2 with a yield of 83%;

[0044] 2) Add compound 2 (10.1g, 0.1mol), 80mL of deionized water, and 30g of acetic acid into the flask under ice-water bath conditions. After the addition is complete, slowly add 8.3g (0.12mol) of sodium nitrite. After the addition is complete, TLC monitors Reaction, the reaction temperature is 0-5°C, and the reaction time is 8h. After the reaction is com...

Embodiment 3

[0046] This embodiment provides a synthetic method of 1,2,4-oxadiazole-3,5-dione, comprising the following steps:

[0047]1) Add compound 1 (10.3g, 0.1mol) and 200mL 1mol / L sodium hydroxide or potassium hydroxide aqueous solution into the flask under ice-water bath conditions, after the addition is complete, slowly add 30% hydrogen peroxide (18.2g) dropwise for 1h After the left and right additions are completed, react at 0°C for 45 minutes, adjust the pH to 4.5 with hydrochloric acid, a white precipitate appears, filter, and recrystallize the filter cake with pure water to obtain compound 2 with a yield of 89%;

[0048] 2) Add compound 2 (10.1g, 0.1mol), 120mL of deionized water, and 50g of acetic acid into the flask under ice-water bath conditions. After the addition, slowly add 11, 1g (0.16mol) of sodium nitrite. Monitor the reaction, the reaction temperature is 0-5°C, and the reaction time is 8 hours. After the reaction is completed, the reaction solution is placed in the ...

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Abstract

The invention relates to a synthesis method of 1, 2, 4-oxadiazole-3, 5-diketone. The method comprises the following steps: placing a reaction mixed solution of a compound 1 and an alkali solution in a reaction system, adding an oxidizing agent, reacting for a period of time, adjusting the pH to be acidic, performing filtering, and recrystallizing a filter cake to obtain a compound 2; and placing the compound 2, an inorganic solvent and an organic solvent in a reaction system, adding nitrite for a reaction, and after the reaction is finished, performing filtering and recrystallization to obtain the target compound 1, 2, 4-oxadiazole-3, 5-diketone. According to the method, the raw materials are few in variety and easy to obtain; reaction conditions are mild; compared with a synthesis method in the literature 2, the provided method has less three-waste emission and fewer steps; and hydroxylamine is used in the literature 2, and the requirement for equipment in industrial production is strict, while the hydroxylamine does not need to be used in the method, the process is simple, and the requirement for the equipment is low.

Description

technical field [0001] The invention belongs to the field of synthesis of organic compounds, and relates to a synthesis method of 1,2,4-oxadiazole-3,5-dione with simple process, suitable reaction conditions, low production cost, fast reaction rate and high yield . Background technique [0002] Oxadiazoledione, its formula C 2 h 2 N 2 o 2 O, its structural formula is shown in S-1, the pure product is white to off-white solid. The compound is used as an important organic intermediate for pharmaceutical intermediates. [0003] [0004] At present, the synthetic methods of 1,2,4-oxadiazole-3,5-dione mainly contain the following types: [0005] 1) According to the literature (Archiv der Pharmazie, 1981, vol.314, #4, p.294-302) report: 1-methylhydrazine-formamide is used as raw material, THF is used as solvent, and benzoyl chloride occurs at reflux temperature Condensation reaction, followed by ring closure reaction under alkaline conditions, the yield is 51%. The disadv...

Claims

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Application Information

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IPC IPC(8): C07D271/07C07C273/02
CPCC07D271/07C07C273/02
Inventor 赖依峰张冬林李渊贞
Owner HANGZHOU KAIMING PANGDE BIOTECH CO LTD
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