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

A technology of calcium malonate and its application is applied in the preparation of 2-substituted malonate calcium salt and the application field of calcium salt, which can solve problems such as affecting product purity, shorten the time for recovering or concentrating solvent, prevent decomposition, The effect of simple operation of the separation process

Inactive Publication Date: 2007-01-31
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

[0032] 48.4g (0.2mol) of 2-thiophenol diethyl malonate was added to 120g of 20% potassium hydroxide aqueous solution, and hydrolyzed at 90-95° C. for 1-2 hours with TLC (developing solvent: ethyl acetate). : petroleum ether = 1: 5) showed that the spot of the raw material basically disappeared as the reaction end point. Add 65 mL of water and cool to 5°C, add concentrated hydrochloric acid to adjust pH to 6.5, add 0.24 mol of calcium chloride aqueous solution to precipitate a large amount of solid. After filtration, the filter cake was washed with water and methanol, and dried to obtain 39.9 g of white powdery solid of calcium 2-thiophenol malonate with a yield of 89% and a purity of 99.2%.

Embodiment 2

[0034] 48.4g (0.2mol) of 2-thiophenol diethyl malonate was added to 120g of 20% potassium hydroxide aqueous solution, and hydrolyzed at 90-95° C. for 1-2 hours with TLC (developing solvent: ethyl acetate). : petroleum ether = 1: 5) showed that the spot of the raw material basically disappeared as the reaction end point. 65 mL of water was added and cooled to 40° C., and concentrated hydrochloric acid was added to adjust the pH to 7.0, and 0.2 mol of calcium chloride aqueous solution was added to precipitate a large amount of solid. After filtration, the filter cake was washed with water and methanol, and dried to obtain 30.6 g of white powdery solid of calcium 2-thiophenol malonate with a yield of 68.3% and a purity of 99.3%.

Embodiment 3

[0036] 48.4g (0.2mol) of 2-thiophene diethyl malonate was added to 100g of 20% aqueous sodium hydroxide solution, hydrolyzed at 90-95° C. : petroleum ether = 1: 5) showed that the spot of the raw material basically disappeared as the reaction end point. 65 mL of water was added and cooled to 0 °C, and concentrated hydrochloric acid was added to adjust the pH to 6.3, and 0.3 mol of calcium chloride aqueous solution was added to precipitate a large amount of solid. Filter, wash the filter cake with water and methanol, and dry to obtain 37.5 g of white powdery solid of calcium 2-thiophenol malonate 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 the application of the calcium salt. Background technique [0002] 2-Substituted malonic acid such as 2-(thiophenol-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] Formula I [0005] At present, the compound of formula I is usually prepared by 2-substituted cyanoacetate or 2-substituted malonate through alkali hydrolysis, acidification, extraction and purification (European Patent 21645; US Patent 3502656). Because the compound of formula I is very water-soluble, is more sensitive to heat and acid, and is easily decomposed, if the solvent extraction method is used to prepare, there are mainly the following shortcomings: (a) a large amount of organic s...

Claims

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Application Information

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IPC IPC(8): C07D333/24C07C57/36C07C57/34
Inventor 马启明王具明
Owner 马启明
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