A kind of secondary/tertiary amide compound and its synthetic method

A technology for 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 direct reaction, high yield and good universality Effect

Active Publication Date: 2021-05-18
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • 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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  • A kind of secondary/tertiary amide compound and its synthetic method
  • A kind of secondary/tertiary amide compound and its synthetic method
  • A kind of secondary/tertiary amide compound and its synthetic method

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 and figure 2 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ7.86(d, J=7.3H...

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 and Figure 4 Shown, product NMR characterization: 1 H...

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 and F...

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Abstract

The invention discloses a secondary / tertiary amide compound and a synthesis method thereof. Adding aryl silane and amine compounds, catalysts and additives to a solvent, and then introducing CO under a certain pressure for carbonylation reaction, and then separating and purifying the compound. This gives secondary / tertiary amides. The method for preparing secondary / tertiary amides by carbonylation reaction of the present invention is simple and efficient, has direct reaction, high atom economy, and wide and stable substrate sources. The reaction system of the invention does not require inert gas protection, and the conditions are mild. Under optimized reaction conditions, the target product is easy to separate, and the yield is as high as 92%.

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 Patents(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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