Preparation method of 2 substituted calcium malonate and use of calcium salt

A technology for calcium malonate and its use, which is applied in the field of preparation of 2-substituted calcium malonate and the application of calcium salt, can solve problems affecting product purity, achieve shortened recovery or concentrated solvent time, low solubility, The effect of simple operation of the separation process

Inactive Publication Date: 2008-07-16
马启明
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the compound of formula I is very water-soluble, sensitive to heat and acid, and easy to decompose, if it is prepared by solvent extraction, it mainly has the following disadvantages: (a) a large amount of organic solvent is needed to extract the compound of formula I from the aqueous solution of hydrolysis; (b) A small amount of compound of formula I will be decomposed to produce monoacid compound during long-time recovery and concentrated solvent, which will affect the purity of the product; (c) if you want to obtain a compound of formula I with high purity, use the method in US Patent 3502656 to refine , need to use the big benzene of toxicity to make solvent; And adopt the method described among the European Patent 21645 to need to use a large amount of ether and dichloromethane to make solvent

Method used

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  • Preparation method of 2 substituted calcium malonate and use of calcium salt
  • Preparation method of 2 substituted calcium malonate and use of calcium salt
  • Preparation method of 2 substituted calcium malonate and use of calcium salt

Examples

Experimental program
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Effect test

Embodiment 1

[0029] 48.4g (0.2mol) of 2-thiophene diethyl malonate was added to 120g of 20% potassium hydroxide aqueous solution, and was hydrolyzed at 90-95°C for 1-2 hours, and TLC (developing agent: ethyl acetate : Petroleum ether=1:5) shows that the raw material spot basically disappears as the reaction end point. Add 65mL of water and cool to 5°C, add concentrated hydrochloric acid to adjust the pH to 6.5, add 0.24mol calcium chloride aqueous solution to precipitate a large amount of solids. Filter, wash the filter cake with water and methanol, and dry to obtain 39.9 g of 2-thiophene calcium malonate white powdery solid, with a yield of 89% and a purity of 99.2%.

Embodiment 2

[0031] 48.4g (0.2mol) of 2-thiophene diethyl malonate was added to 120g of 20% potassium hydroxide aqueous solution, and was hydrolyzed at 90-95°C for 1-2 hours, and TLC (developing agent: ethyl acetate : Petroleum ether=1:5) shows that the raw material spot basically disappears as the reaction end point. Add 65mL of water and cool to 40°C, add concentrated hydrochloric acid to adjust the pH to 7.0, add 0.2mol calcium chloride aqueous solution to precipitate a large amount of solids. Filter, wash the filter cake with water and methanol, and dry to obtain 30.6 g of 2-thiophene calcium malonate white powdery solid, with a yield of 68.3% and a purity of 99.3%.

Embodiment 3

[0033] 48.4g (0.2mol) of 2-thiophene diethyl malonate was added to 100g of 20% sodium hydroxide aqueous solution, and was hydrolyzed at 90-95°C for 2-4 hours, and was analyzed by TLC (developing agent: ethyl acetate : Petroleum ether=1:5) shows that the raw material spot basically disappears as the reaction end point. Add 65mL of water and cool to 0°C, add concentrated hydrochloric acid to adjust the pH to 6.3, add 0.3mol calcium chloride aqueous solution to precipitate a large amount of solids. Filter, wash the filter cake with water and methanol, and dry to obtain 37.5 g of 2-thiophene calcium malonate white powdery solid, with a yield of 83.7% and a purity of 99.1%.

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Abstract

The present invention discloses a preparation method of 2-substituted calcium malonate salt and its application. Said invention also provides its reaction formula and concrete steps of its preparation method. The invented 2-substituted calcium malonate salt can be used for preparing 2-(thiophene-3) malonic acid or 2-phenylmalonic acid.

Description

technical field [0001] The invention relates to a preparation method for obtaining high-purity 2-substituted malonate calcium salt and an application of the calcium salt. Background technique [0002] 2-Substituted malonic acid such as 2-(thiophene-3) malonic acid or 2-phenylmalonic acid is an important intermediate of broad-spectrum semi-synthetic penicillin antibiotics, such as ticarcillin or carbenicillin, such as formula I, wherein R is thiophen-3-yl or phenyl. [0003] [0004] At present, the compound of formula I is usually prepared by 2-substituted cyanoacetate or 2-substituted malonate through alkaline hydrolysis, acidification, extraction and purification (European Patent 21645; US Patent 3502656). Because the compound of formula I is very water-soluble, sensitive to heat and acid, and easy to decompose, if it is prepared by solvent extraction, it mainly has the following disadvantages: (a) a large amount of organic solvent is needed to extract the compound of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/24C07C57/36C07C57/34
Inventor 马启明王具明
Owner 马启明
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