Method for preparing 3-(2-hydroxyethyl)-2-oxazolidone

A technology of oxazolidinone and hydroxyethyl, which is applied in the field of catalytic synthesis of fine chemical products, can solve the problems of many research results, and achieve the effects of high activity, stable properties, and easy separation and recovery

Active Publication Date: 2014-08-06
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of catalytic systems, the synthesis of oxazolidinones from aziridine and carbon dioxide is far less researched than the synthesis of cyclic carbonates from epoxy compounds.

Method used

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  • Method for preparing 3-(2-hydroxyethyl)-2-oxazolidone
  • Method for preparing 3-(2-hydroxyethyl)-2-oxazolidone
  • Method for preparing 3-(2-hydroxyethyl)-2-oxazolidone

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Experimental program
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Embodiment 1

[0032] Measure 0.046g (0.2mmol) of catalyst 2,2',2"-terpyridine shown in formula III-1, 0.174g (2mmol) of compound 1-(2-hydroxyethyl) ethyleneimine shown in formula II and Add 6mL of organic solvent ethanol into a 25-mL stainless steel autoclave. After sealing the autoclave, fill it with carbon dioxide with a pressure of 30atm at 25°C. Stir and heat to 90°C. Keep warm for cyclization reaction for 20h. Then cool To room temperature, release gas.Reaction result: the yield of 3-(2-hydroxyethyl)-2-oxazolidinone is 58%.

[0033]

[0034] The proton nuclear magnetic spectrum of the product obtained in this embodiment is as figure 1 As shown, the carbon spectrum as figure 2 As can be seen from the figure, the product has a correct structure and is 3-(2-hydroxyethyl)-2-oxazolidinone shown in formula I.

Embodiment 2

[0036] Measure 0.046g (0.2mmol) of 2,2',2"-terpyridine, 0.174g (2mmol) of 1-(2-hydroxyethyl) ethyleneimine and 6mL methanol into a 25-mL stainless steel autoclave In. After sealing the reactor, fill it with 30atm carbon dioxide at 25°C. Stir and heat to 110°C. Keep warm for cyclization reaction for 20h. Then cool to room temperature and release gas. Reaction result: 3-(2-hydroxyethyl The yield of -2-oxazolidinone was 70%.

[0037] The NMR results of the product obtained in this embodiment are exactly the same as in Example 1, and will not be repeated here.

Embodiment 3

[0039] Measure 0.046g (0.2mmol) of 2,2',2"-terpyridine, 0.174g (2mmol) of 1-(2-hydroxyethyl) ethyleneimine and 6mL methanol into a 25-mL stainless steel autoclave In. After sealing the reactor, fill it with 30atm carbon dioxide at 25°C. Stir and heat to 130°C. Keep warm for cyclization reaction for 20h. Then cool to room temperature and release gas. Reaction result: 3-(2-hydroxyethyl The yield of -2-oxazolidinone was 60%.

[0040] The NMR results of the product obtained in this embodiment are exactly the same as in Example 1, and will not be repeated here.

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Abstract

The invention discloses a method for preparing 3-(2-hydroxyethyl)-2-oxazolidone. The method comprises a step of by taking a nitrogen-containing compound as a catalyst, carrying out a cyclization reaction on a compound 1-(2-hydroxyethyl) ethylenimine shown in formula II in atmosphere of carbon dioxide to obtain the compound 3-(2-hydroxyethyl)-2-oxazolidone shown in formula I. By using non-metal nitrogen-containing organic molecules as a catalyst system, the method disclosed by the invention effectively avoids pollution of metal ions on finished oxazolidone due to use of a metal catalyst, and is cheap and easily available; the adopted catalyst, which is stable non-metal organic molecules, can be recycled, and the catalyst system is environmentally friendly.

Description

technical field [0001] The invention belongs to the field of catalytic synthesis of fine chemical products, and relates to a method for preparing 3-(2-hydroxyethyl)-2-oxazolidinone. Background technique [0002] Oxazolidinones are a very important class of five-membered heterocyclic compounds, and they are chiral auxiliary agents and reaction intermediates in organic synthesis and polymer synthesis. In addition, oxazolidinones are often used as biologically active reagents and are widely used in the fields of medicine and agriculture. [0003] Example: Linezolid, the first clinically used oxazolidinone antibacterial agent. Based on the importance of oxazolidinones, it is very meaningful to develop new processes for efficient and green synthesis of oxazolidinones. [0004] At present, the industrial synthesis methods of relatively mature oxazolidinone mainly contain the following three kinds: the carbonylation reaction of aminoalcohols and phosgene or carbon monoxide, the d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/22
CPCY02P20/584C07D263/22
Inventor 华瑞茂刘慧鑫
Owner TSINGHUA UNIV
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