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A kind of preparation method of 5-nitrofurfural and nifuratel

A technology of nitrofurfural and nitro, which is applied in the field of preparation of 5-nitrofurfural and nifuratel, can solve the problem of low yield and purity of 5-nitrofurfural, low total yield of nifuratel, easy Generate polymers and other problems, achieve the effect of less impurities, shorten reaction time, and reduce side reactions

Active Publication Date: 2019-01-29
CHENGDU QINGSHAN LIKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In the prior art, 5-nitrofurfural diethyl ester and dilute acid are hydrolyzed in organic alcohol to prepare 5-nitrofurfural; then 5-nitrofurfural and N-amino-5-methylthio Nylmethyl-2-oxazolidinone is carried out condensation reaction, prepares nifuratel; In the process of this method preparation 5-nitrofurfural, side reaction is more, easily generates polymer, and there are many impurities in the reaction product, 5 - The yield and purity of nitrofurfural is low, thus resulting in a low overall yield of nifuratel

Method used

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  • A kind of preparation method of 5-nitrofurfural and nifuratel
  • A kind of preparation method of 5-nitrofurfural and nifuratel
  • A kind of preparation method of 5-nitrofurfural and nifuratel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Preparation of 5-nitrofurfural (compound 2)

[0050]

[0051] In a 100L reactor, add ethanol 60L, 5-nitrofurfural diethyl ester (compound 1) 20kg (82.25mol), 10% sulfuric acid (m / v) 1.5L, indium trichloride 910.06g (4.11mol), Heated to 80-85°C, reacted for 1.5h, concentrated under reduced pressure to remove ethanol to obtain a concentrate; the concentrate was dissolved in dichloromethane, washed three times with saturated sodium chloride, and the dichloromethane layer was collected; Dry over sodium sulfate, filter to remove the solid sodium sulfate, concentrate under reduced pressure to obtain the crude product of 5-nitrofurfural; the crude product is purified by silica gel column chromatography (eluent PE:EA=5:1), collect the target substance, and concentrate under reduced pressure , to obtain pure 5-nitrofurfural with a purity of 98% and a yield of 82%.

[0052] Adopt high performance liquid chromatography (HPLC) to detect the 5-nitrofurfural pure product that...

Embodiment 2

[0067] (1) Preparation of 5-nitrofurfural (compound 2)

[0068] In a 100L reactor, add ethanol 60L, 5-nitrofurfural diethyl ester (compound 1) 20kg (82.25mol), 10% sulfuric acid (m / v) 1.5L, InCl 3 / HC(OEt) 3 (indium trichloride 4.11mol, InCl 3 with HC(OEt) 3 The molar ratio is 1:0.5), heated to 78-85°C, reacted for 1h, concentrated under reduced pressure to remove ethanol, and obtained the concentrate; the concentrate was dissolved in dichloromethane, washed three times with saturated sodium chloride, and the dichloromethane was collected layer; the dichloromethane layer was dried with anhydrous sodium sulfate, filtered to remove the sodium sulfate solid, and concentrated under reduced pressure to obtain the crude product of 5-nitrofurfural; the crude product was purified by silica gel column chromatography (eluent PE:EA=5:1) , collect the target substance, and concentrate under reduced pressure to obtain the pure product of 5-nitrofurfural with a yield of 69.3%.

[0069] ...

Embodiment 3

[0075] (1) Preparation of 5-nitrofurfural (compound 2)

[0076] In a 100L reactor, add ethanol 60L, 5-nitrofurfural diethyl ester (compound 1) 20kg (82.25mol), 10% sulfuric acid (m / v) 1.5L, InCl 3 / HC(OEt) 3 (4.11mol, InCl 3 with HC(OEt) 3 The molar ratio is 1:1.0), heated to 78-85°C, reacted for 1.5h, concentrated under reduced pressure to remove ethanol to obtain a concentrate; the concentrate was dissolved in dichloromethane, washed three times with saturated sodium chloride, and collected dichloro The methane layer; the dichloromethane layer was dried with anhydrous sodium sulfate, filtered to remove the sodium sulfate solid, and concentrated under reduced pressure to obtain the crude product of 5-nitrofurfural; the crude product was purified by silica gel column chromatography (eluent PE:EA=5:1 ), collect the target substance, and concentrate under reduced pressure to obtain the pure product of 5-nitrofurfural with a yield of 89.2%.

[0077] If nifuratel is prepared, ...

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Abstract

The invention discloses a method for preparing 5-nitro-2-furaldehyde. The method comprises the following steps: a) 5-nitryl furfural ester diacetate, low alcohol, inorganic acid, lewis acid or a mixture of the above components are subjected to a reaction for 1-2 hours at the temperature of 70-90 DEG C to obtain a reaction solution containing 5-nitro-2-furaldehyde; b) removing low alcohol from the reaction solution in the step a) through vacuum concentration to obtain a concentrate; dissolving the concentrate by dichloromethane, washing the concentrate, drying the concentrate, performing vacuum concentration to obtain a crude product; and c) purifying the crude product in the step b) through silica-gel column chromatography to obtain 5-nitro-2-furaldehyde. The method has the advantages of less side reaction and short reaction time, and can increase the yield and purity of the 5-nitro-2-furaldehyde. The prepared 5-nitro-2-furaldehyde has the advantages that impurity is little, purifying treatment is not required, the 5-nitro-2-furaldehyde can be directly used for preparing nifuratel, preparation operation steps of nifuratel are simplified, and the yield and the purity of nifuratel are increased.

Description

technical field [0001] The invention relates to a preparation method of 5-nitrofurfural and nifuratel. Background technique [0002] 5-nitro-furfural (5-nitro-2-furaldehyde) is an important chemical intermediate, which can be used to synthesize nifuratel, nifurdizone, furanguanidine, nifurone, furoxanone, furazolidone and other drugs, the structure of which is shown in Formula I. [0003] [0004] Nifuratel (Nifuratel), chemical name: 5-[(methylthio)methyl]-3-[[(5-nitro-2-furan)methylene]amino]-2-oxazolidinone (5-[(Methylthio)methyl]-3-[[(5-nitro-2-furanyl)methylene]amino]-2-oxazolidinone), its structure is shown in formula Ⅱ, for G + , G - , protozoa, mold, chlamydia, mycoplasma, etc. all have a strong killing effect. Trichomonas, vaginal infections caused by Candida albicans and other diseases. [0005] [0006] At present, the preparation methods of 5-nitrofurfural and nifuratel include: [0007] (1) Chinese patent CN 102863434 A discloses a synthetic method o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/71C07D413/12
Inventor 徐世兰张韬范琴欧苏朱勇刘小英
Owner CHENGDU QINGSHAN LIKANG PHARMA CO LTD