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Method for synthesizing carbamic ester through alkyl boronic acid, amine and carbon dioxide

A carbamate, hydrocarbyl boronic acid technology, applied in the preparation of carbamate derivatives, organic chemistry methods, chemical instruments and methods, etc., can solve problems such as life-threatening safety and environmental pollution, and achieve safe, simple and adaptable reaction operations. The effect of good and good industrial application prospects

Active Publication Date: 2015-11-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The aromatic chloroformate, carbamoyl chloride and isocyanate used in the above three methods all have relatively high toxicity, and most of them are prepared by phosgene, which may cause environmental pollution and seriously threaten people's life safety in the production process.

Method used

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  • Method for synthesizing carbamic ester through alkyl boronic acid, amine and carbon dioxide
  • Method for synthesizing carbamic ester through alkyl boronic acid, amine and carbon dioxide
  • Method for synthesizing carbamic ester through alkyl boronic acid, amine and carbon dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 0.5 mmol phenylboronic acid, 0.2 mmol cuprous oxide, 3 ml dichloromethane, 2.5 mmol diethylamine, 1.5 mmol boron trifluoride diethyl ether, 1.5 mmol pyridine to the autoclave, first fill 0.4 Oxygen in MPa, and then filled with carbon dioxide to make the total pressure reach 4MPa. After stirring and reacting at 80°C for 24 hours, stop heating and stirring, cool to room temperature, and slowly vent unreacted CO 2 . The reaction solution was extracted with ethyl acetate, filtered, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, which was then separated and purified by column chromatography to obtain the target product. The eluent of the column chromatography used was petroleum ether with a volume ratio of 20:1 : ethyl acetate mixed solvent, productive rate 61%.

Embodiment 2

[0038] Add 0.5 mmol phenylboronic acid, 0.2 mmol cuprous oxide, 3 ml dichloromethane, 2.5 mmol diethylamine, 1 mmol boron trifluoride diethyl ether, 1.5 mmol pyridine to the autoclave, and first fill 0.4 Oxygen in MPa, and then filled with carbon dioxide to make the total pressure reach 4MPa. After stirring and reacting at 80°C for 24 hours, stop heating and stirring, cool to room temperature, and slowly vent unreacted CO 2. The reaction solution was extracted with ethyl acetate, filtered, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, which was then separated and purified by column chromatography to obtain the target product. The eluent of the column chromatography used was petroleum ether with a volume ratio of 20:1 : ethyl acetate mixed solvent, productive rate 39%.

Embodiment 3

[0040] Add 0.5 mmol phenylboronic acid, 0.05 mmol cuprous oxide, 3 ml dichloromethane, 2.5 mmol diethylamine, 1.5 mmol boron trifluoride diethyl ether, 1.5 mmol pyridine into the autoclave, and first fill 0.2 Oxygen in MPa, and then filled with carbon dioxide to make the total pressure reach 4MPa. After stirring and reacting at 80°C for 24 hours, stop heating and stirring, cool to room temperature, and slowly vent unreacted CO 2 . The reaction solution was extracted with ethyl acetate, filtered, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, which was then separated and purified by column chromatography to obtain the target product. The eluent of the column chromatography used was petroleum ether with a volume ratio of 20:1 : ethyl acetate mixed solvent, productive rate 78%.

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Abstract

The invention belongs to the technical field of medical and chemical synthesis and discloses a method for synthesizing carbamic ester through alkyl boronic acid, amine and carbon dioxide. The synthesizing method includes the steps that the alkyl boronic acid, the amine and a solvent are added in a pressure-resistant reactor, cuprous oxide is added as a catalyst, alkali is added as a ligand, boron trifluoride diethyl etherate is added as an additive, oxygen and carbon dioxide are introduced, stirring reaction is carried out for 6-24 hours at the temperature of 40-120 DEG C, the mixture is cooled to room temperature after the reaction is finished, after reaction liquid is filtered, pressure is reduced, the solvent is steamed away, a rough product is obtained, and column chromatography and purification are carried out on the rough product to obtain the carbamic ester. The raw materials used in the synthesizing method are non-toxic or low in toxin, low in price and easy to obtain, reaction operation is safe and easy, adaptability to functional groups is good, adaptability to a substrate is wide, and the method has good industrial application prospects.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and in particular relates to a method for synthesizing carbamate by using hydrocarbyl boronic acid, amine and carbon dioxide. Background technique [0002] Carbamate compounds as a class of nitrogen-containing oxygen-containing compounds (general formula R 1 R 2 NCOOR 3 ), which have important biological activities. It has very important applications in agricultural production and is widely used as insecticides, acaricides, herbicides and fungicides, etc. According to chemical properties, carbamate pesticides can be divided into N-methyl carbamate (such as carbaryl), N, N-dimethyl carbamate (such as pirimicarb) and carbamate oxime ester (such as Methomyl) and other three categories. Secondly, carbamates are also widely used in medicine. For example, the drug Prezista for the treatment of AIDS and the drug VESIcare for the treatment of bladder spasm are carbamate com...

Claims

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Application Information

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IPC IPC(8): C07B43/00C07C269/04C07C271/44C07C271/34C07C319/20C07C323/20C07D295/205
Inventor 戚朝荣熊文芳江焕峰
Owner SOUTH CHINA UNIV OF TECH
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