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Method for synthetizing carbamate

A carbamate and synthetic method technology, applied in the field of synthetic carbamate, can solve the problems of threatening human safety, high toxicity and explosion, environmental pollution, etc., and achieve the reduction of environmental hazards, non-toxic raw materials, and environmental friendliness Effect

Active Publication Date: 2015-02-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Traditionally, carbamates are synthesized from phosgene or isocyanate substances. Because phosgene or isocyanate substances are highly toxic and explosive, they are likely to cause environmental pollution during use and seriously threaten human safety. Therefore, they are used in industrial applications. are greatly restricted in (S.Ozaki, Chem.Rev.1972,72,457-496; R.A.Batey, V.Santhakumar, C.Y.Ishii, S.D.Taylor, Tetrahedron Lett.1998,39,6267-6270)

Method used

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  • Method for synthetizing carbamate
  • Method for synthetizing carbamate
  • Method for synthetizing carbamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add 0.5 mmol of p-bromoacetophenone p-toluenesulfonylhydrazone, 0.5 mmol of tetrahydropyrrole, 0.5 mmol of potassium carbonate, 3 ml of acetonitrile, and fill with 0.5 MPa of CO in the autoclave. 2 , after stirring and reacting at 50°C for 6 hours, stop heating and stirring, cool to room temperature, and slowly vent unreacted CO 2 . The reaction solution was filtered, and the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product. Rate 8%.

Embodiment 2

[0044] Add 0.5 mmol of p-bromoacetophenone p-toluenesulfonylhydrazone, 10 mmol of tetrahydropyrrole, 2.5 mmol of potassium carbonate, 6 ml of acetonitrile, and fill with 10 MPa of CO in the autoclave. 2 , after stirring and reacting at 150°C for 72 hours, stop heating and stirring, cool to room temperature, and slowly vent unreacted CO 2. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product. rate 58%.

Embodiment 3

[0046] Add 0.5 mmol of p-bromoacetophenone p-toluenesulfonylhydrazone, 5 mmol of tetrahydropyrrole, 1 mmol of potassium carbonate, 3 ml of acetonitrile, and fill with 6 MPa of CO in the autoclave. 2 , after stirring and reacting at 120°C for 24 hours, stop heating and stirring, cool to room temperature, and slowly vent unreacted CO 2 . The reaction solution was filtered, and the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product. rate 49%.

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Abstract

The invention relates to a method for synthetizing carbamate. The method comprises the following steps: adding sulfonyl hydrazones, amine and solvents in a high-pressure kettle, adding alkali as an accelerant, introducing carbon dioxide, performing a stirring reaction for 6-72 hours at the temperature of 40-150 DEG C, cooling the high-pressure kettle to the room temperature after the reaction is completed, slowly releasing carbon dioxide which is not reacted to constant pressure, filtering a reaction liquid, decompressing and stewing the solvents to obtain crude products, and obtaining a series of carbamate chemical compounds through refining in a column chromatography. The method for synthetizing carbamate is safe and simple to operate, the prices of raw materials are low, the raw materials are easy to obtain, the adaptability for functional groups is high, the adaptability for substrates is wide, the method is environmental-friendly, industrial production is facilitated, and the method is widely applied to the synthesis of agricultural chemicals, medicines and natural products.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a method for synthesizing carbamate. Background technique [0002] Carbamates are a class of nitrogen-containing compounds with biological and pharmaceutical activity, and are widely used as pesticides such as insecticides and herbicides. Carbamate is also an important skeleton structure for building natural products and drugs. For example, brand-name drugs sold on the market such as Prezista, Lunesta, Xeloda, and VESIcare contain carbamate fragments. In addition, carbamate compounds are also an important class of raw materials and intermediates, and have important uses in organic synthesis. Therefore, the synthesis of carbamates has been receiving extensive attention. [0003] Traditionally, carbamates are synthesized from phosgene or isocyanate substances. Because phosgene or isocyanate substances are highly toxic and explosive, they are likely to ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/00C07D295/205C07C269/00C07C271/12
Inventor 戚朝荣熊文芳江焕峰任颜卫
Owner SOUTH CHINA UNIV OF TECH
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