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Method for preparing 5-nitro-2-furaldehyde and nifuratel

A technology of nitrofurfural and nitro group is applied in the field of preparation of 5-nitrofurfural and nifuratel, and can solve the problems of low yield and purity of 5-nitrofurfural, low total yield of nifuratel and easy Problems such as the formation of polymers, to achieve the effect of less impurities, shortened reaction time, and reduced side reactions

Active Publication Date: 2016-08-03
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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  • Method for preparing 5-nitro-2-furaldehyde and nifuratel
  • Method for preparing 5-nitro-2-furaldehyde and nifuratel

Examples

Experimental program
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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 preparation method of 5-nitrofurfural, which comprises the following steps: a. 5-nitrofurfural diethyl ester, lower alcohol, inorganic acid, Lewis acid or a mixture thereof are reacted at 70°C to 90°C 1h to 2h to obtain a reaction solution containing 5-nitrofurfural; b. The reaction solution in step a is concentrated under reduced pressure to remove lower alcohols to obtain a concentrate; the obtained concentrate is dissolved in dichloromethane, washed, dried, and concentrated under reduced pressure , to obtain a crude product; c, the crude product of step b was purified by silica gel column chromatography to obtain 5-nitrofurfural. The method of the present invention has few side reactions, short reaction time, and improves the yield and purity of 5-nitrofurfural; the 5-nitrofurfural prepared by the present invention has few impurities and can be directly used to prepare nifurate without purification treatment Er, simplified the operation steps of preparing nifuratel, further improved the yield and the purity of nifuratel.

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 CN102863434A discloses a kind of synthetic me...

Claims

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Application Information

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Patent Type & Authority Applications(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
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