Method for synthesizing oxazoline-2-ketone

A technology for synthesizing oxazoline and oxazoline, which is applied in organic chemistry and other fields, can solve the problems of difficult separation of catalysts and products, and achieve the effects of large-scale industrial production, low corrosion, and easy subsequent separation

Inactive Publication Date: 2011-05-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The product selectivity of this method reaches more than 99%, no racemization occurs on the chiral substrate, both the selenium catalyst and the solvent can be recycled, and the catalytic activity is basically unchanged, which solves the difficulty of separating the catalyst and the product in homogeneous catalysis

Method used

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  • Method for synthesizing oxazoline-2-ketone
  • Method for synthesizing oxazoline-2-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 10ml of acetonitrile, 0.61g (10mmol) of ethanolamine, 0.0395g (0.5mmol) of Se into a three-necked flask, put it in an oil bath that has been heated to 30°C, stir and react with carbon monoxide for about 15 minutes to approximately equal the volume of CO 10 Oxygen was introduced at a rate of %, and the reaction was stirred for 8h. Stop CO, continue to oxidize with oxygen for 2 hours, filter and recover the catalyst, and evaporate the solvent in vacuum to obtain the crude product. After purification by recrystallization, the product is weighed to obtain 0.84 g of oxazoline-2-one. The first single pass yield is 93. % (Based on ethanolamine).

Embodiment 2

[0028] The organic solvent is dimethylformamide, and the experimental method and steps are the same as those in Example 1. The first single pass yield is 85% (calculated as ethanolamine).

Embodiment 3

[0030] The organic solvent is pyridine, and the experimental method and steps are the same as in Example 1. The first single-pass yield is 93% (calculated as ethanolamine).

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Abstract

A method for synthesizing or substituting oxazoline-2-ketone comprises the steps of performing cyclocarbonylation with beta-amino alcohols as reactant and CO as carbonylation reagent and in the presence of selenium catalyst to obtain oxazoline-2-ketone, wherein the molar ratio of selenium catalyst and the reactant is 1-20% (mol), the reaction time is 2-20 hours, the reaction temperature is 10-100DEG C, and the CO pressure is 1atm. By using the inventive method, the product has selectivity over 99% and has no racemization to chiral substrates, both the selenium catalyst and the solvent can berecycled, and the catalytic activity is substantially unchanged, so as to solve the difficulty of difficult separation of a catalyst and a product in a homogeneous catalysis.

Description

Technical field [0001] The invention relates to a method for synthesizing fine chemicals oxazoline-2-one compounds, in particular to a method for catalytically synthesizing oxazoline-2-one compounds instead of phosgene or phosgene derivatives. Background technique [0002] Oxazoline-2-one, especially chiral oxazoline-2-one, is a class of fine chemicals widely used in pesticides, medicine, synthesis and other fields. At present, the synthesis of this type of compound mainly adopts the phosgene method or the phosgene derivative method. Since the phosgene method or the phosgene derivative method uses highly toxic phosgene, a large amount of highly corrosive chlorine-containing by-products are produced during the reaction. , Causing serious corrosion of the equipment, which is an environmental pollutant. In recent years, with the strengthening of people's environmental awareness, environmental protection standards have been raised, and environmentally friendly synthesis methods have...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/20
Inventor 李鹏陆世维原晓华俞俊学王树东
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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