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Synthetic process of furan ammonium salt

A technology of furan ammonium salt and synthesis process, applied in the direction of organic chemistry, etc., can solve the problem of low conversion rate of furanone acid, achieve the effects of improving yield and purity, reducing production cost, and reducing content

Active Publication Date: 2017-08-25
SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Further, the present invention adopts the reaction temperature of oximation of 58-60 DEG C, and the formation rate of furoic acid is less than 1%, which greatly improves the yield of the product, but the conversion rate of furanonic acid is relatively low

Method used

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  • Synthetic process of furan ammonium salt

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Mix and stir 100mL water and 150g 2-acetylfuran, control the temperature at 30°C, slowly add sodium nitrite aqueous solution (prepared by mixing 113g sodium nitrite and 153mL water) dropwise, after the dropwise addition, add concentrated hydrochloric acid ( The mass fraction is 36%) to adjust the pH value to 2.0 to obtain a furanonic acid solution, and the liquid phase detection shows that the conversion rate is 97.5%;

[0028] (2) Add 300 g of anhydrous methanol to the obtained furanone acid solution, and control the temperature of the solution to 35 ° C. At the same time, add 3 drops of concentrated sulfuric acid to the mixed solution, and react for 2.0 h under stirring. After the reaction is completed, distill the reaction solution , remove excess methyl alcohol, obtain furanonic acid methyl ester;

[0029] (3) Lower the temperature to 20°C, add 110 g of methoxyamine dropwise to the obtained methyl furanone, adjust the pH to 2.0, react for 1.5 hours, and detect b...

Embodiment 2

[0033] (1) Mix and stir 200mL of water and 306g of 2-acetylfuran, control the temperature at 0°C, slowly add an aqueous solution of sodium nitrite (prepared by mixing 282g of sodium nitrite and 312mL of water), and after the addition is complete, add concentrated hydrochloric acid ( The mass fraction is 36%) to adjust the pH value to 3.0 to obtain a furanonic acid solution, and the liquid phase detection shows that the conversion rate is 98.7%;

[0034] (2) Add 650g of absolute ethanol to the obtained furanone acid solution and control the temperature of the solution to 37°C. At the same time, add 3 drops of concentrated sulfuric acid to the mixed solution, and react for 1.2h under stirring. After the reaction is completed, distill the reaction solution , remove excess ethanol, obtain ethyl furanone;

[0035] (3) Lower the temperature to 30°C, add 230 g of methoxyamine dropwise to the obtained ethyl furanone, adjust the pH to 4.0, react for 2.6 hours, detect in liquid phase, t...

Embodiment 3

[0039] (1) Mix and stir 50mL water and 40g 2-acetylfuran, control the temperature at 78°C, slowly add sodium nitrite aqueous solution (prepared by mixing 50g sodium nitrite and 68mL water) dropwise, after the dropwise addition, add concentrated hydrochloric acid ( The mass fraction is 36%) to adjust the pH value to 2.0 to obtain a furanonic acid solution, and the liquid phase detection shows that the conversion rate is 96.1%;

[0040] (2) Add 90g of anhydrous methanol to the obtained furanone acid solution and control the temperature of the solution to be 32°C. At the same time, add 3 drops of concentrated sulfuric acid dropwise to the mixed solution and react for 5h under stirring. After the reaction is completed, distill the reaction solution to remove Excessive methyl alcohol, obtains methyl furanone;

[0041] (3) Lower the temperature to 30°C, add 48 g of methoxyamine dropwise to the obtained methyl furanone, adjust the pH to 4.0, react for 2.6 hours, detect in liquid phas...

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Abstract

The invention belongs to the technical field of medical intermediate preparation, and particularly relates to a synthetic technology of furan ammonium salt. The synthetic technology comprises the steps that 2-acetyl furan is used as a raw material to form furanone acid through oxidative synthesis at first, then esterification is performed, the product reacts with methoxyamine to be synthesized into a methoxy group oximation product, the methoxy group oximation product is hydrolyzed and then reacts with an alcohol amine solvent, and the furan ammonium salt is obtained. Due to the fact that the furanone acid is esterified at first, the carbonyl activity is improved, and more oximation products are promoted to be converted into cis-form products. The content of the obtained anti-form furan ammonium salt is only 5-8%; compared with a traditional furan ammonium salt production method, the content of the anti-form furan ammonium salt is obviously reduced without lowering productivity.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical intermediates, and in particular relates to a synthesis process of furan ammonium salt. Background technique [0002] Cefuroxime is a semi-synthetic broad-spectrum cephalosporin antibiotic for parenteral administration. Ammonium furan is one of the important intermediates of cefuroxime. [0003] Patent 200810121255.8 relates to the preparation method of furan ammonium salt. The method is to add 2-oxo-2-furyl acetic acid and water into the reaction vessel, adjust the pH value with inorganic acid, and then add methoxyamine aqueous solution or its hydrochloride Aqueous solution; heat preservation reaction, controlled by inorganic base and inorganic acid in the reaction process, adjusting the pH value of the reaction solution with inorganic acid, then extracting and merging the organic layer with organic solvent; feeding ammonia gas or liquid ammonia into the organic layer, filt...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/54
CPCC07D307/54
Inventor 郑庚修赵攀峰刘庆东赵承彪刘悦
Owner SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD
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