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Method for synthesizing trifluoromethyl-containing carbamate by using carbon dioxide

A carbamate and trifluoromethyl technology, which is applied in the fields of chemical industry, medicine, and organic synthesis, can solve the problems of carbamate compounds being less reported, and achieve high yield of target products, safe and simple operation, and easy-to-obtain raw materials Effect

Active Publication Date: 2017-09-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the research on the synthesis of carbamates using carbon dioxide has made great progress, there are few reports on the direct synthesis of carbamate compounds containing trifluoromethyl groups using carbon dioxide as raw materials.

Method used

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  • Method for synthesizing trifluoromethyl-containing carbamate by using carbon dioxide
  • Method for synthesizing trifluoromethyl-containing carbamate by using carbon dioxide
  • Method for synthesizing trifluoromethyl-containing carbamate by using carbon dioxide

Examples

Experimental program
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Effect test

Embodiment 1

[0050] Add 1.5 ml dimethyl sulfoxide, 0.20 mmol phenylacetylene, 1.0 mmol diisobutylamine, 0.24 mmol 1-trifluoromethyl-1,2-phenyliodyl-3(1H )-ketone, then add 0.02 mmol copper acetate and 0.04 mmol 1,10-phenanthroline, then fill with 4MPa carbon dioxide, stir and react at 60°C for 8 hours, stop heating and stirring, cool to room temperature, and release slowly Release carbon dioxide to atmospheric pressure. The reaction solution was washed with 10 mL of water, extracted three times with ethyl acetate (15 mL each time), the organic phases were combined and dried over anhydrous magnesium sulfate, concentrated by distillation under reduced pressure to obtain a crude product, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 2:1, and the yield was 76%.

Embodiment 2

[0052] Add 1.5 ml dimethyl sulfoxide, 0.20 mmol phenylacetylene, 1.0 mmol diisobutylamine, 0.24 mmol 1-trifluoromethyl-1,2-phenyliodyl-3(1H )-ketone, then add 0.02 mmol copper trifluoromethanesulfonate, 0.04 mmol 1,10-phenanthroline, then fill with 4MPa carbon dioxide, stir and react at 60°C for 8 hours, stop heating and stirring, and cool to At room temperature, slowly release carbon dioxide to normal pressure. The reaction solution was washed with 10 mL of water, extracted three times with ethyl acetate (15 mL each time), the organic phases were combined and dried over anhydrous magnesium sulfate, concentrated by distillation under reduced pressure to obtain a crude product, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 2:1, and the yield was 71%.

Embodiment 3

[0054] Add 1.5 ml dimethyl sulfoxide, 0.20 mmol phenylacetylene, 1.0 mmol diisobutylamine, 0.24 mmol 1-trifluoromethyl-1,2-phenyliodyl-3(1H )-ketone, then add 0.02 mmol copper acetate, 0.04 mmol 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, then fill with 4 MPa of carbon dioxide, stir at 60 ° C After reacting for 8 hours, stop heating and stirring, cool to room temperature, and slowly release carbon dioxide to normal pressure. The reaction solution was washed with 10 mL of water, extracted three times with ethyl acetate (15 mL each time), the organic phases were combined and dried over anhydrous magnesium sulfate, concentrated by distillation under reduced pressure to obtain a crude product, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 2:1, and the yield was 70%.

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Abstract

The invention relates to a method for synthesizing trifluoromethyl-containing carbamate by using carbon dioxide. The method comprises the steps of sequentially adding an organic solvent, alkyne, amine and a Togni reagent into a high-pressure reaction kettle, and then adding copper salt serving as a catalyst and an organic compound containing nitrogen or phosphor serving as a ligand; after that, replenishing the high-pressure reaction kettle with carbon dioxide, and stirring for carrying out a reaction for 5-24h at the temperature of 40-80 DEG C; after the reaction is finished, cooling to the room temperature, slowly discharging carbon dioxide to normal pressure, washing reaction liquid with water, extracting by using ethyl acetate, drying by using anhydrous magnesium sulfate, and then carrying out reduced pressure distillation and concentration to obtain a crude product; then, purifying by means of column chromatography to obtain a trifluoromethyl-containing carbamate compound. The method for synthesizing the trifluoromethyl-containing carbamate has the advantages of being easy in obtaining of raw materials, safe and simple in operation, mild in reaction conditions, good in functional group compatibility, wide in substrate applicability, high in yield of target product, and the like, is beneficial to industrial production, and has potential application prospect in synthesis of pesticides and medicines.

Description

technical field [0001] The invention relates to the technical fields of organic synthesis, medicine and chemical industry, in particular to a method for synthesizing trifluoromethyl-containing carbamate by utilizing carbon dioxide. Background technique [0002] Fluorine-containing organic compounds are playing an increasingly important role in various fields of life science, high-tech industry and national defense industry. Statistics show that currently 20% of medicines and 30% of pesticides contain at least one fluorine atom. While trifluoromethyl (-CF 3 ) due to its strong electron-withdrawing properties, lipophilicity, and stable carbon-fluorine bonds, introducing it into organic compounds can significantly change the polarity, lipophilicity, and chemical and metabolic stability of the compound, so it contains trifluoromethyl The compounds have been widely used in the fields of pesticides, medicine and materials. For example, the drug Januvia for the treatment of type...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/12C07C269/04C07C269/08C07D333/16C07D295/20
CPCC07C269/04C07C269/08C07D295/20C07D333/16C07C271/12
Inventor 戚朝荣郭天佐汪露江焕峰
Owner SOUTH CHINA UNIV OF TECH
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