N-aryl secondary aryl amide synthetic method
A technology for the synthesis of aryl secondary aromatic amides and methods, which is applied in the field of synthesis of N-aryl secondary aromatic amides, can solve the problems of harsh reaction conditions, many by-products, cumbersome steps, etc., and achieve the effect of high yield and easy separation
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Embodiment 1
[0053] Preparation of N-phenylbenzamide
[0054] Dissolve 1 mmol of phenylboronic acid in a reactor containing 5 mL of anisole, add 1 mmol of aniline under stirring, and dissolve with 0.05 mmol of Pd(dppf)Cl 2 As the main catalyst, 0.05mmol copper powder is used as the co-catalyst, CO is introduced into the reaction system to make the pressure of the reaction system 3MPa, heated and stirred at 100°C for 24 hours, and the progress of the reaction is monitored by TLC. After the reaction is complete, it is concentrated and passed through the column Chromatographic separation, to obtain 158mg white solid, yield rate is 80%, and the product structure formula is as follows:
[0055]
[0056] Such as figure 1 and figure 2 Shown, product NMR characterization: 1 H-NMR (400MHz, DMSO-d 6 )δ10.27 (s,1H),8.00–7.91(m,3H),7.78(d,J=7.6Hz,2H),7.65–7.49(m,3H),7.36(t,J=7.9Hz,2H ),7.11(t,J=7.4Hz,1H). 13 C-NMR (101MHz, DMSO-d 6 )δ 165.50, 139.12, 134.94, 131.51, 128.56, 128.34, 127.60, ...
Embodiment 2
[0058] Preparation of 3-methyl-N-phenylbenzamide
[0059] Dissolve 2mmol of m-tolylboronic acid in a 5mL DMF reactor, add 1mmol of aniline under stirring, use 0.2mmol of palladium chloride as the main catalyst, and 0.2mmol of cuprous chloride as the cocatalyst, and pass through the reaction system Enter CO to make the pressure of the reaction system 2MPa, heat and stir at 130°C for 24 hours, monitor the progress of the reaction with TLC, concentrate after the completion of the reaction, and separate through column chromatography to obtain 171mg of white solid with a yield of 81%. The structural formula is as follows:
[0060]
[0061] Such as image 3 and Figure 4 Shown, product NMR characterization: 1 H-NMR (400MHz, DMSO-d 6 )δ 10.21(s,1H),7.78(s,1H),7.83–7.72(m,3H),7.47–7.31(m,4H),7.10(t,J=7.4 Hz,1H),2.41(s, 3H). 13 C-NMR (101MHz, DMSO-d 6 )δ165.61, 139.18, 137.64, 134.96, 132.06, 128.54, 128.23, 128.08, 124.77, 123.54, 120.27, 20.94.
Embodiment 3
[0063] Preparation of 4-ethyl-N-phenylbenzamide
[0064] Dissolve 1mmol of p-ethylphenylboronic acid in a reactor containing 5mL of n-hexane, add 1mmol of aniline under stirring, use 0.05mmol of palladium acetate as the main catalyst, and 0.05mmol of cuprous iodide as a cocatalyst, and add to the reaction system Feed CO to make the pressure of the reaction system 5 MPa, heat and stir at 30 ° C for 24 hours, monitor the progress of the reaction with TLC, concentrate after the completion of the reaction, and separate by column chromatography to obtain 191 mg of white solid with a yield of 85%. The product structure is as follows:
[0065]
[0066] Such as Figure 5 and Figure 6 Shown, product NMR characterization: 1 H-NMR (400MHz, Chloroform-d) δ 7.81(s,1H),7.79(s,1H),7.70–7.59(m,2H),7.41–7.34(m,2H),7.31(d,J=8.3 Hz, 2H), 7.20–7.10(m, 1H), 2.72(q, J=7.6Hz, 2H), 1.27(t, J=7.6Hz, 3H). 13 C-NMR (101MHz, Chloroform-d) δ165.19, 148.13, 137.54, 131.85, 128.59, 127.79, 126.62, ...
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