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Method for synthesizing (z)-2-(alpha-methoxyimino)furan-ammonium acetate

A technology of ammonium furanoacetate and methoxyimide, applied in the direction of organic chemistry and the like, can solve problems such as unfriendly operating environment and unsatisfactory yield, and achieve the effects of reducing operating links, reducing costs, and improving operating environment

Active Publication Date: 2009-02-04
JIANGSU QINGQUAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] A large amount of ethanol is used as the reaction solvent in the preparation process of the above two ammonium furan salts, resulting in unfriendly operating environment and unsatisfactory yield

Method used

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  • Method for synthesizing (z)-2-(alpha-methoxyimino)furan-ammonium acetate
  • Method for synthesizing (z)-2-(alpha-methoxyimino)furan-ammonium acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 14.0g (0.1mol) of 99.0% 2-oxo-2-furyl acetic acid, 100mL water, and add 31% hydrochloric acid to adjust the pH to 3.5~4, add 47g of 12% methoxyamine aqueous solution (methoxyamine purity 98%) (0.12mol) at 15~20°C, then keep warm at 20~25°C for 4h, use liquid caustic soda and Hydrochloric acid controls the pH to 3.5-4; after the reaction, adjust the pH of the reaction solution to 0.2 with 31% hydrochloric acid at 15-20°C, then extract it with 100mL chloroform three times, wash the organic layer with saturated brine, dry, and filter; Slowly inject ammonia gas into the organic layer at 5-10°C for about 4 hours until the pH is 7, then keep it warm for 1 hour, and filter to obtain 15.6 g of the crude product; add the crude product to 60 g of methanol, add 2 g of activated carbon, and heat up to reflux for 1 hour , Filtrate while hot to remove activated carbon, then concentrate the mother liquor, distill off about 45g of methanol and cool to 0-5°C, crystallize to give 14....

Embodiment 2

[0034] The methoxyamine aqueous solution is changed into adding methoxyamine hydrochloride 9.2g (0.11mol) in batches, and adds 30% liquid caustic soda of 14.6g, and other is with embodiment 1, the result obtains product 15.1g, yield 81.1%, The liquid phase purity is 99.2%, and the infrared spectrogram is the same as in Example 1.

Embodiment 3

[0036] The amount of water added was changed to 150mL, and the others were the same as in Example 1. As a result, 15.0g of the product was obtained, with a yield of 80.6%, and a liquid phase purity of 99.0%. The infrared spectrogram was the same as in Example 1.

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Abstract

The invention relates to a method for synthesizing (z)-2-(alpha-methoxy imine) furan ammonium acetate, comprising the following method: 2-oxo-2-furyl acetate and water are added into a vessel, the PH is adjusted by inorganic acid, and then methoxamine solution or the hydrochloride solution thereof are added; insulating reaction is carried out, inorganic base and inorganic acid are used for controlling in the reaction process, the PH of the reaction solution is adjusted by the inorganic acid, and organic layers are extracted and combined by an organic solvent; alkaline air or liquid ammonia is pumped into the organic layers, and crude product is obtained after filtration and centrifugation; the crude product is added into refining solvent, active carbon is added to decolorize, heating reflux is carried out, the active carbon is filtered and removed before getting cold, then mother solution is concentrated, cooled and crystallized, thus obtaining the product. The synthesizing method reduces cost and operation steps and improves the yield rate.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis methods, in particular to a method for synthesizing (z)-2-(alpha-methoxyimine)ammonium furanacetate. Background technique [0002] (z)-2-(α-methoxyimine) ammonium furan acetate or 2-(z)-methoxyimine-2-furan ammonium acetate, also known as furan ammonium salt, is used in the synthesis of cefuroxime axetil key intermediates. The methods currently used for the synthesis of (z)-2-(α-methoxyimine) ammonium furan acetate mainly contain: [0003] Shandong Chemical Industry, 34(6), 5-8, 2005 introduced that oximation reaction of 2-oxo-2-furan acetic acid and methoxyamine was carried out, and then ammonia gas was introduced to obtain the product. The reaction formula is as follows: [0004] [0005] This process uses ethanol as a solvent to control the pH of the reaction to 5-6, the molar ratio of methoxyamine to 2-oxo-2-furan acetic acid is about 1.2, and the reaction temperature is about ...

Claims

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Application Information

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IPC IPC(8): C07D307/54
Inventor 王平潘伟平应素华王凌云张浩钟李慧徐卫军
Owner JIANGSU QINGQUAN CHEM CO LTD
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