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Preparing method of 2-methoxy imino group 2-furan ammonium acetate

A technology of methoxyimino and amine furanoacetate is applied in the field of preparation of 2-methoxyimino-2-furanoacetate amine, and can solve the problems of many types of solvents, large amount of by-product furoic acid, large solvent consumption and the like , to reduce costs and improve yields

Inactive Publication Date: 2009-09-23
ZHEJIANG TOP MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many types of solvents in the production process, and the solvent consumption is large
At the same time, the temperature of oximation and rearrangement leads to a large amount of by-product furoic acid, about 5-15%.

Method used

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  • Preparing method of 2-methoxy imino group 2-furan ammonium acetate
  • Preparing method of 2-methoxy imino group 2-furan ammonium acetate

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Embodiment Construction

[0019] A detailed description will be given below of specific embodiments of the present invention.

[0020] The preparation method of 2-methoxyimino 2-furan acetate amine, the method comprises the following steps:

[0021] ①. Reaction of sodium nitrite and furan acetate, the reaction temperature is 59°C±1°C, and furanonic acid is generated through oximation, rearrangement, and hydrolysis;

[0022] ②, add hydrochloric acid, adjust the pH to 0.2, use butyl acetate to extract, then add Na 2 CO 3 Solution stripping obtains furanone acid;

[0023] ③. Condensation of furanone acid and methoxyammonium hydrochloride to generate 2-imino 2-furan acetic acid;

[0024] ④, adjust the pH to 0.5, use butyl acetate to extract 2-imino-2-furanacetic acid, add activated carbon for dehydration and decolorization;

[0025] ⑤. Add methanol with solvent volume of 5-10% in the reaction solution, and then pass ammonia gas to form a salt to generate 2-methoxyimino 2-furanacetate amine.

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Abstract

The invention relates to a preparing method of 2-methoxy imino group 2-furan ammonium acetate which comprises the following steps: (1) sodium nitrite reacts with acetate furan to generate furan keto acid by oximation, rearrangement and hydrolysis; (2) the furan keto acid is extracted; (3) condensation reaction is carried out on the furan keto and methoxy ammonium hydrochloride to generate 2-imino group 2-furan acetic acid; (4) the 2-imino group 2-furan acetic acid is extracted; (5) ammonia is introduced for salt formation to generate the 2-methoxy imino group 2-furan ammonium acetate; wherein, solvent adopted in the furan keto extraction of step (2) is butyl acetate. Under the same condition, the dissolution loss of the ethyl acetate in water is four times larger than that of the butyl acetate. With the butyl acetate being adopted as the solvent, the unit consumption is lowered by 50 percent, and the production cost is lowered. Furthermore, 58-60 DEG C of the reaction temperature for oximation is adopted by the invention, the production rate of furoic acid is smaller than 1 percent, and the product yield is improved greatly.

Description

technical field [0001] The invention relates to a preparation method of 2-methoxyimino 2-furan acetic acid amine. Background technique [0002] 2-Methoxyimino 2-furanoacetate amine (SMIA) is the 7-position side chain of cefuroxime, and is an important intermediate for the synthesis of cephalosporin drug - cefuroxime axetil. Its main synthetic routes are: use 2-furocarboxylic acid as raw material to generate 2-furoyl chloride through chlorination, or use 2-acetylfuran as raw material to generate 2-furoyl chloride through chlorination, and then undergo cyanolysis and hydrolysis , Prepared by oximation. As in "Synthesis of 2-methoxyimine 2-furan ammonium acetate" (Journal of Jiangxi Medical College, Volume 43, No. 3, 2003), the above-mentioned route yield is not high, and strong corrosive oxychloride is used in the synthesis process. Sulfone and highly toxic cyanide are therefore not suitable for industrial production. [0003] "Synthesis of (S)-2-methoxyimino-2-furan acetic...

Claims

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Application Information

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IPC IPC(8): C07D307/54
Inventor 姚凤鸣
Owner ZHEJIANG TOP MEDICINE
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