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Carbon dioxide one-pot method for directly preparing oxazolidine-2-one compounds

A ketone compound, carbon dioxide technology, applied in the direction of organic chemistry, can solve the problem of high raw material price, achieve the effect of low raw material price, enhanced electrophilicity, and low price

Inactive Publication Date: 2014-02-12
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All of the above-mentioned non-phosgene methods have the disadvantage of high raw material prices

Method used

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  • Carbon dioxide one-pot method for directly preparing oxazolidine-2-one compounds
  • Carbon dioxide one-pot method for directly preparing oxazolidine-2-one compounds
  • Carbon dioxide one-pot method for directly preparing oxazolidine-2-one compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: 1-butyl-3-methylimidazole acetate ([Bmim]OAc) catalyzes propylene oxide, CO 2 Preparation of 5-methyl-3-phenyloxazolidin-2-one by one-pot method with aniline

[0026]The first step is to add ionic liquid 1-butyl-3-methylimidazole acetate ([Bmim]OAc) (0.8mmol, 0.159g) and the ring represented by formula (I) into a 50ml autoclave with magnetic stirring. Oxypropane (40mmol, 2.323g), filled with CO at room temperature 2 To the initial pressure of 2.5MPa, heated to 110 ° C for 6 hours. The autoclave was cooled to room temperature and reduced to normal pressure, and the reaction solution was transferred to a 5 mL round bottom flask. The second step adds aniline (2mmol, 0.186g) shown in formula (II), N 2 The reaction was continued at 140° C. for 9 hours under protection. After the reaction, cool to room temperature, use petroleum ether / ethyl acetate = 3:1 as the developer column chromatography, and vacuum dry to obtain 5-methyl-3-phenyloxazolidine- 2-ketone ...

Embodiment 2

[0028] Embodiment 2: 1-butyl-3-methylimidazole acetate ([Bmim]OAc) catalyzes epichlorohydrin, CO 2 One-pot preparation of 5-chloromethyl-3-phenyloxazolidin-2-one with aniline

[0029] In the preparation method of this example, the epoxy compound is epichlorohydrin (40mmol, 3.700g) shown in formula (I), and other preparation conditions and methods are the same as in Example 1, and 5-chlorohydrin shown in formula (III) is prepared. Methyl-3-phenyloxazolidin-2-one 0.423 g, yield 99%.

[0030]

Embodiment 3

[0031] Embodiment 3: 1-butyl-3-methylimidazole acetate ([Bmim]OAc) catalyzes propylene oxide, CO 2 One-pot preparation of 3-(4-chlorophenyl)-5-methyl-oxazolidin-2-one with p-chloroaniline

[0032] In the preparation method of this example, aniline or aniline derivatives are p-chloroaniline (2mmol, 0.255g) shown in formula (II), and other preparation conditions and methods are the same as in Example 1, and 3-chloroaniline shown in formula (III) is prepared. (4-Chlorophenyl)-5-methyl-oxazolidin-2-one 0.389 g, yield 92%.

[0033]

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PUM

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Abstract

The invention discloses a carbon dioxide one-pot method for directly preparing oxazolidine-2-one compounds. The method comprises the following steps: adding a catalytic amount of ionic liquid into epoxy compounds, carrying out reactions under a primary pressure of CO2, then adding aniline or aniline derivatives, and making the reactions going on so as to prepare the oxazolidine-2-one compounds. The carbon dioxide one-pot method has the advantages of no need to separate intermediate products, little using amount of catalyst, safe reaction operation, mild reaction conditions, no addition of any organic solvent in the reaction process, and environment-friendliness.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis methods, and in particular relates to a method for directly preparing oxazolidin-2-one compounds by a carbon dioxide one-pot method. Background technique [0002] CO 2 is the main greenhouse gas on earth, reducing CO 2 Emissions are a major strategic issue for governments, science and industry today. However, with the growth of the world population and the improvement of modernization, the human demand for energy is increasing rapidly, which inevitably causes CO 2 increase in emissions; therefore, how to minimize CO 2 At the same time as the emission, the enriched CO 2 The transformation of resources into energy, materials and fine chemical products has attracted the attention of many scientists (Science in China: Chemistry 41 (2011) 925-932). [0003] The "one-pot method" is a promising organic synthesis method. The multi-step reaction in the one-pot reaction can directly obtain m...

Claims

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Application Information

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IPC IPC(8): C07D263/22C07D263/20
CPCC07D263/22C07D263/20
Inventor 高国华王滨燊杨四娟张利锋
Owner EAST CHINA NORMAL UNIV
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