One-pot method for synthesizing N-substituted phthalimide through carbonylation

A phthalimide, carbonylation reaction technology, applied in organic chemistry and other directions, can solve problems such as poor atom economy, high-pressure reaction conditions, etc., and achieve the effects of excellent yield, simple operation, and good adaptability of functional groups

Active Publication Date: 2015-12-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above carbonylation methods for the construction of N-substituted phthalimides all use amides or aryl halides as reaction substrates. The disadvantages are that the raw materials need to be prepared in advance, high-pressure reaction conditions are required, and atom economy is poor.

Method used

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  • One-pot method for synthesizing N-substituted phthalimide through carbonylation
  • One-pot method for synthesizing N-substituted phthalimide through carbonylation
  • One-pot method for synthesizing N-substituted phthalimide through carbonylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Add 0.2 mmol of benzaldehyde, 0.4 mmol of tert-butylamine, 0.01 mmol of palladium chloride, 0.2 mmol of copper oxide into a 25 mL test tube, add 3 ml of toluene (PhMe) and N,N-dimethylformamide (DMF) As a mixed solvent, the volume ratio was 10:1, and stirred at room temperature for 12 hours. Then put on a balloon containing carbon monoxide and oxygen as a carbonyl source, and stir at 100 degrees Celsius. After the TLC (thin layer chromatography) detection reaction, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. 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 55%.

Embodiment 2

[0056] Add 0.2 mmol of benzaldehyde, 0.4 mmol of tert-butylamine, 0.01 mmol of bistriphenylphosphine palladium dichloride, 0.2 mmol of copper oxide into a 25 mL test tube, add toluene (PhMe) and N,N-dimethylformaldehyde Amide (DMF) 3 ml was used as a mixed solvent with a volume ratio of 10:1, and stirred at room temperature for 12 hours. Then put on a balloon containing carbon monoxide and oxygen as a carbonyl source, and stir at 100 degrees Celsius. After the TLC (thin layer chromatography) detection reaction, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. 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 21%.

Embodiment 3

[0058] Add 0.2 mmoles of benzaldehyde, 0.4 mmoles of tert-butylamine, 0.01 mmoles of palladium dichlorodiacetonitrile, 0.2 mmoles of copper oxide into a 25 mL test tube, add toluene (PhMe) and N,N-dimethylformamide (DMF) As a mixed solvent, the volume ratio was 10:1, and stirred at room temperature for 12 hours. Then put on a balloon containing carbon monoxide and oxygen as a carbonyl source, and stir at 100 degrees Celsius. After the TLC (thin layer chromatography) detection reaction, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. 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 of 67%.

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Abstract

The invention relates to a one-pot method for synthesizing N-substituted phthalimide through carbonylation. The method comprises the following steps: adding aromatic aldehyde, amine, a metal palladium catalyst and a solvent into a reaction container, then adding a copper salt as an oxidizing agent and carrying out stirring for 4 to 24 h at normal temperature; sleeving the reaction container with a balloon filled with carbon monoxide and oxygen and carrying out a stirring reaction at 40 to 150 DEG C for 12 to 72 h; after completion of the reaction, carrying out cooling to room temperature and dismounting the balloon; subjecting a reaction solution to filtering and carrying out pressure reduced evaporation to remove a solvent so as to obtain a crude product; and subjecting the crude product to column chromatographic purification so as to obtain the N-substituted phthalimide. The one-pot method for synthesizing N-substituted phthalimide through carbonylation is simple and safe to operate, uses easily available and cheap raw materials, has good function group applicability and can be used for synthesis of a plurality of drug molecules; and the method has excellent yield, is favorable for industrial production and has important application values in organic synthesis.

Description

technical field [0001] The invention relates to the technical fields of organic chemical industry, pharmaceutical synthesis, material chemistry, etc., and specifically relates to a method for synthesizing substituted phthalimides in one pot using carbonylation reaction Background technique [0002] As an important fine chemical intermediate, N-substituted phthalimide is widely used in medicine, optoelectronic materials, pesticides, dyes and other industries. [0003] In the field of medicine, N-substituted phthalimide and its derivatives are important intermediates in the process of pharmaceutical production, which can be used to synthesize various antibacterial and antitumor drugs, and are of great importance to medical research. significance. For example, N-bromoethylphthalimide and N-chloroethylphthalimide can be used as painkillers and anti-inflammatory drugs. N-glycosyl-substituted phthalimides can be anticancer and anti-tumor drugs, which shows the important value of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07D209/66
CPCC07D209/48C07D209/66
Inventor 江焕峰及方华伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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