Secondary/tertiary amide compound and synthesis method thereof

A technology of amine compounds and synthesis methods, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid amides, etc., can solve problems such as harsh reaction conditions, and achieve the effects of direct reaction, high yield, and wide sources

Active Publication Date: 2019-01-11
SHAANXI UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods often require harsh reaction conditions, such as reaction under acidic or high temperature conditions.

Method used

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  • Secondary/tertiary amide compound and synthesis method thereof
  • Secondary/tertiary amide compound and synthesis method thereof
  • Secondary/tertiary amide compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Preparation of N-(p-tolyl)benzamide

[0069] 0.75mmol of trimethoxyphenylsilane, 10mol%Pd(PPh 3 ) Cl 2 and 2equiv.CuF 2 dissolved in 3mLCH 3 In the Shrek tube of CN (equipped with a magnetic stirrer), close the reaction tube, pass carbon monoxide from the branch of the reaction tube, make it full of balloons and then empty them, repeat three times until the air in them is completely emptied, and then put Fill the balloon, then add 0.5mmol p-methylaniline into the reaction tube, heat and stir at 80°C for 24 hours, monitor the progress of the reaction with TLC, extract three times with 10mL ethyl acetate after the reaction is complete, combine the organic phases and concentrate , separated by silica gel column chromatography to obtain 97.1 mg of white solid compound, the yield rate is 92%, and the product structure formula is as follows:

[0070]

[0071] Such as figure 1 with figure 2 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ7.86(d, J=7....

Embodiment 2

[0074] Preparation of N-(4-methoxyphenyl)benzamide

[0075] 0.75mmol of trimethoxyphenylsilane, 10mol%Pd(PPh 3 ) Cl 2 and 2equiv.CuF 2 dissolved in 3mLCH 3 In the Shrek tube of CN (equipped with a magnetic stirrer), close the reaction tube, pass carbon monoxide from the branch of the reaction tube, make it full of balloons and then empty them, repeat three times until the air in them is completely emptied, and then put Fill the balloon, then add 0.5mmol of p-methoxyaniline into the reaction tube, heat and stir at 80°C for 24 hours, monitor the progress of the reaction with TLC, extract three times with 10mL ethyl acetate after the reaction is complete, combine the organic phases and carry out Concentrate and separate through silica gel column chromatography to obtain 94.3 mg of white solid compound with a yield of 83%. The structural formula of the product obtained is as follows:

[0076]

[0077] Such as image 3 with Figure 4 Shown, product NMR characterization: 1...

Embodiment 3

[0080] Preparation of N-(4-fluorophenyl)benzamide

[0081] 0.75mmol of trimethoxyphenylsilane, 10mol%Pd(PPh 3 ) Cl 2 and 2equiv.CuF 2 dissolved in 3mLCH 3 In the Shrek tube of CN (equipped with a magnetic stirrer), close the reaction tube, pass carbon monoxide from the branch of the reaction tube, make it full of balloons and then empty them, repeat three times until the air in them is completely emptied, and then put The balloon was filled, and then 0.5 mmol of p-fluoroaniline was added to the reaction tube, heated and stirred at 80°C for 24 hours, and the progress of the reaction was monitored by TLC. After the reaction was complete, it was extracted three times with 10 mL of ethyl acetate, and the combined organic phases were concentrated. After separation by silica gel column chromatography, 87.1 mg of white solid compound was obtained, with a yield of 81%, and the structural formula of the product obtained was as follows:

[0082]

[0083] Such as Figure 5 with ...

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Abstract

The invention discloses a secondary/tertiary amide compound and a synthesis method thereof. The method comprises the following steps: adding arylsilane and an amine compound, a catalyst and an additive to a solvent, introducing CO under a certain pressure, carrying out a carbonylation reaction, and carrying out separation and purification to obtain the secondary/tertiary amide. The method for preparing the secondary/tertiary amide by the carbonylation reaction has the advantages of concision, high efficiency, directness in the reaction, high atom economy, and wide sources and good stability ofa substrate. The reaction system of the invention does not require inert gas protection, and has mild conditions, and the target product is easy to separate and the yield reaches up to 92% under optimized reaction conditions.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a secondary / tertiary amide compound and a synthesis method thereof. Background technique [0002] Amide compounds widely exist in natural products and drug molecules, and are an important class of chemical skeletons. Traditional synthesis of amides is based on the condensation of amines and carboxylic acid derivatives [a) Constable, D.J.C.; Dunn, P.J.; Hayler, J.D.; Humphrey, G.R.; Leazer, J.J.L.; Linderman, R.J.; Lorenz, K. ; Manley, J.; Pearlman, B.A.; Wells, A.; Zaks, A.; Zhang, T.Y. Green Chem.2007, 9, 411-420.b) Wu, X.-F.; Chem. 2007, 72, 765-774.]. However, such methods often require harsh reaction conditions, such as reaction under acidic or high temperature conditions. In recent years, there have been many novel methods for the synthesis of amides, such as using halogenated hydrocarbons, arylboronic acids, etc. as substrates, [c) Langer, P., et al.Synthesis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/65C07C233/75C07C233/66C07C231/10C07D295/192C07D209/08
CPCC07C231/10C07C233/65C07C233/66C07C233/75C07D209/08C07D295/192C07C2601/14
Inventor 张金侯艳艳马养民
Owner SHAANXI UNIV OF SCI & TECH
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