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Method for preparing 3-acetamidofuran and derivatives thereof from marine waste biomass

A technology for acetamidofuran and waste biomass, applied in directions such as organic chemistry, can solve problems such as 3-acetamidofuran being rarely reported, and achieve the effects of widening the scope of effective utilization, improving economy, and being easy to operate

Active Publication Date: 2020-05-12
南京奥凯索生物技术有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no matter the pyrolysis reaction or the degradation in the solvent, there are few reports on 3-acetylaminofuran.

Method used

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  • Method for preparing 3-acetamidofuran and derivatives thereof from marine waste biomass
  • Method for preparing 3-acetamidofuran and derivatives thereof from marine waste biomass
  • Method for preparing 3-acetamidofuran and derivatives thereof from marine waste biomass

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Take 0.22g of N-acetylglucosamine, 0.15g of barium hydroxide octahydrate, 0.12g of boric acid, and 0.10g of sodium chloride in a thick-walled pressure-resistant tube, add 10mL of N-methylpyrrolidone to dissolve, protect it with nitrogen, and keep it in a constant temperature oil bath Heat and stir at 180°C in the pot for 120 minutes. After the reaction was completed and cooled to room temperature, 0.5 mL of the filtrate was taken, filtered through a nylon microporous membrane, and the content of 3-acetylaminofuran was detected by gas phase, and the yield of the obtained 3-acetylaminofuran was 58%.

Embodiment 2

[0058] Take 0.42g of N-acetylglucosamine, 0.05g of lithium hydroxide monohydrate, 0.15g of fluorophenylboronic acid, and 0.22g of calcium chloride in a round bottom flask, protect it with nitrogen, and add 10mL of N,N-dimethylformamide , heated at 190°C in a constant temperature oil bath with stirring and reflux for 100 minutes. After the reaction was completed and cooled to room temperature, 0.5 mL of the filtrate was taken, filtered through a nylon microporous membrane, and the content of 3-acetylaminofuran was detected by gas phase. Under the current assay conditions, the yield of 3-acetylaminofuran obtained was 40%.

Embodiment 3

[0060] Take 0.8g of chitin, 0.3g of potassium carbonate, 0.35g of chlorophenylboronic acid, and 0.12g of choline chloride in a thick-walled pressure-resistant tube, protect it with nitrogen, add 10mL of N,N-dimethylacetamide to dissolve, and keep the temperature Heat and stir at 200°C in an oil bath for 150 minutes. After the reaction was completed and cooled to room temperature, 0.5 mL of the filtrate was taken, filtered through a nylon microporous membrane, and the content of 3-acetylaminofuran was detected by gas phase. Under the current assay conditions, the yield of 3-acetylaminofuran obtained was 12%. When chitin is used as a reaction raw material, because it needs to be depolymerized and hydrolyzed into N-acetylglucosamine first, the yield of 3-acetylaminofuran is lower than that of using N-acetylglucosamine as a raw material.

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Abstract

The invention discloses a method for preparing 3-acetamidofuran and derivatives thereof from marine waste biomass. Marine waste biomass chitin or a degradation product acetylglucosamine of the marinewaste biomass chitin is used as a raw material; under the action of a basic catalyst, cyclization dehydration and deacetylation reaction are performed to form 3-acetamidofuran, and the 3-acetamidofuran is further hydrolyzed to obtain the 3-aminofuran. The target product is prepared from the marine waste biomass, the reaction steps are simple, the raw materials are cheap and renewable, the operation is convenient, the product yield is high, and a new method is provided for utilization of the marine waste biomass.

Description

technical field [0001] The invention relates to the preparation of chemicals, in particular to a preparation method of 3-acetylaminofuran and derivatives thereof. [0002] technical background [0003] 3-Acetamidofuran and its hydrolysis product 3-aminofuran is an important small organic molecule, which is often used in drug synthesis. For example: it is introduced into drug molecules through amide bonds; 3-aminotetrahydrofuran obtained by hydrogenation is applied to the antiarrhythmic drug CVT-510, etc. However, because 3-aminofuran is unstable, it is easy to form an imine resonance structure, so that more side reactions occur, so it appears more often in the form of acyl protection. [0004] Methods for the preparation of 3-acetylfuran or 3-aminofuran have been reported. For example: Granik et al prepared 3-aminofuran derivatives by cyclization of cyanoethers. The group prepared stable polysubstituted 3-aminofuran derivatives by treating cyanovinyl ethers with a strong b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/66
CPCC07D307/66Y02P20/54
Inventor 曹飞冯曹坚武红丽林长渠陈可泉韦萍欧阳平凯
Owner 南京奥凯索生物技术有限公司
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