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Synthesis method of N-aryl amide with recoverable raw materials

The technology of an arylamide and a synthesis method is applied in the field of N-arylamide synthesis with recyclable raw materials, and can solve the problems of high cost of catalyst raw materials, long reaction time, low atom utilization rate and the like

Pending Publication Date: 2021-09-14
周旭明
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current methods for the synthesis of amides still have disadvantages such as low atom utilization, harsh conditions, high cost of catalyst raw materials, and long reaction time.

Method used

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  • Synthesis method of N-aryl amide with recoverable raw materials
  • Synthesis method of N-aryl amide with recoverable raw materials
  • Synthesis method of N-aryl amide with recoverable raw materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] figure 1 A schematic diagram of a recyclable N-arylamide synthetic method is shown, and the specific process is:

[0044] S1: Add 2.4mmol of p-methyliodobenzene, 2.76mmol of mCPBA, 2.76mmol of toluene, and 17mL of dichloromethane into the vacuum reaction flask, then put it in an ice bath at 0°C, and use a rubber-tipped dropper to drop Add 0.6 mL of trifluoromethanesulfonic acid, and stir at room temperature for 12 hours after two hours;

[0045] S2: Continue to add about 5.7mg of Cu(OAc) to S1 2 , 2 mL of DCE, 0.7 mmol of H 2 O and 1.0mmol of benzonitrile are then connected to the vacuum / inert gas manifold system and fed with nitrogen for protection, heated in an oil bath, and the temperature is kept at 80°C, and the reaction is continuously stirred for 20 hours;

[0046] S3: After the reaction is complete, cool to room temperature, filter, and filter out Cu(OAc) 2 , EtOAc was added to the filtrate, stirred for half an hour, and the organic layer was separated. Was...

Embodiment 2

[0050] figure 2 A schematic diagram of a recyclable N-arylamide synthetic method is shown, and the specific process is:

[0051] S1: Add 2.4mmol of 3,4-dimethyliodobenzene, 2.76mmol of mCPBA, 2.76mmol of o-xylene, and 17mL of dichloromethane into a vacuum reaction flask, then put it in an ice bath at 0°C, and use Add 0.6 mL of trifluoromethanesulfonic acid drop by drop with a rubber dropper, and stir at room temperature for 12 hours after two hours;

[0052] S2: Add about 5.7 mg of CuI, 2 mL of DCE, and 0.7 mmol of H to S1 2 O, 1.0 mmol of benzonitrile was connected to the vacuum / inert gas manifold system to feed nitrogen for protection, heating, the temperature was maintained at 75 ° C, and the reaction was continued for 17 hours with stirring;

[0053] S3: The reaction is completed, cooled to room temperature, filtered, and Cu(OAc)2 was filtered out, EtOAc was added to the filtrate, stirred for half an hour, and the organic layer was separated. Wash the organic layer wit...

Embodiment 3

[0057] image 3 A schematic diagram of a recyclable N-arylamide synthetic method is shown, and the specific process is:

[0058] S1: Add 2.4mmol of 4-methoxy-3-methylbenzene, 2.86mmol of mCPBA, 2.76mmol of 2-methylanisole, and 20mL of dichloromethane into a vacuum reaction flask, and then put In an ice bath, add 0.75 mL of trifluoromethanesulfonic acid dropwise using a rubber dropper, and stir at room temperature for 19 hours after two hours;

[0059] S2: Continue to add about 5.7mg of CuI, 2mL of DCE, 0.7mmol of H to S1 2 O, 1.0 mmol of benzonitrile was then connected to the vacuum / inert gas manifold system and fed with nitrogen for protection, heating, the temperature was maintained at 75 ° C, and the reaction was continued for 18 hours with stirring;

[0060] S3: After the reaction is complete, cool to room temperature, filter, and filter out Cu(OAc) 2 , EtOAc was added to the filtrate, stirred for half an hour, and the organic layer was separated. Wash the organic laye...

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Abstract

The invention provides a synthesis method of N-aryl amide with recoverable raw materials, which utilizes the double influence of steric hindrance and electric aromatic hydrocarbon effect on amidation selectivity, so that amidation only occurs at the para-position of an aromatic hydrocarbon electron-rich substituent group, then a single product is prepared accordingly, and the raw material problem of Goldberg reaction and the position selectivity problem of direct C-H bond amidation are solved.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a method for synthesizing N-arylamide with recyclable raw materials. Background technique [0002] Amides are one of the most common compounds among natural bioactive molecules and synthetic organic compounds. The synthesis of amides has important applications in medicinal chemistry, biology, pesticides and polymer synthesis. It is mainly used as an industrial solvent; it is used in the pharmaceutical industry to produce vitamins, hormones, etc.; it is also an important intermediate in organic synthesis; it can be used to produce dimeform in the pesticide industry. [0003] In the field of pharmaceutical chemical synthesis, surveys show that more than a quarter of drugs are amides. It shows that amide compounds have a huge market in drug synthesis, and can synthesize sulfonamide drugs. It is an excellent chemotherapeutic agent and began to be used in the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/26C07C309/66C07C231/06C07C233/65C07C233/75C07C17/361C07C17/383C07C25/02C07C41/18C07C41/42C07C43/225
CPCC07C303/26C07C231/06C07C17/361C07C17/383C07C41/18C07C41/42C07C309/66C07C233/65C07C233/75C07C25/02C07C43/225
Inventor 周旭明张毅林梁嘉麟吴泽杰陈婧张嘉瑶练嘉宏林伟东余梦琪王舜杰
Owner 周旭明
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