Method for preparing amide compound through catalysis of ligand-assisted zirconium oxychloride
A technology of amide compounds and zirconium oxychloride, which is applied to the preparation of organic compounds, chemical instruments and methods, and the preparation of carboxylic acid amides. It can solve the problems of anhydrous and expensive metal amides, and achieve high production efficiency and low production costs. low cost effect
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Embodiment 1
[0037] In a 100 mL round bottom flask, 1.5 g ethyl benzoate and 1.1 g benzylamine were dissolved in n-heptane, and 0.3 g catalyst ZrOCl was added 2 ·8H 2 O and 0.2g 8-hydroxyquinoline were heated to reflux, and the reaction was terminated when there was no ethyl benzoate detected by TLC. After the reaction mixture was removed under reduced pressure to remove n-heptane, 20mL of ethyl acetate was added, suction filtration, washing, concentration, and crystallization to obtain a white solid, the structure of the resulting product is as follows:
[0038] The yield is 89.0%.
[0039] The resulting product was characterized by a Bruker Avance superconducting Fourier digital nuclear magnetic resonance spectrometer. The characterization data are as follows: δ 1 H NMR(400MHz, CDCl 3 )δ7.79,7.78,7.77,7.49,7.47,7.47,7.43,7.41,7.41,7.39,7.39,7.35,7.34,7.30,7.30,7.28,7.25,6.54,4.63,4.62; 13 C NMR(101MHz, CDCl 3 )δ167.39,138.24,134.44,131.53,128.78,128.58,127.90,127.60,126.98,44.14.
Embodiment 2
[0041] In a 100 mL round bottom flask, 1.5 g of butyl benzoate, 1.0 g of benzylamine were dissolved in n-heptane, and 0.3 g of catalyst ZrOCl 2 ·8H 2 O and 0.1 g of catechol were heated to reflux, and the reaction was terminated when there was no ethyl benzoate detected by TLC. After the reaction mixture was removed under reduced pressure to remove n-heptane, 20mL of ethyl acetate was added, suction filtration, washing, concentration, and crystallization to obtain a white solid, the structure of the resulting product is as follows:
[0042] The yield is 81.0%.
[0043] The obtained product was characterized by a Bruker Avance type superconducting Fourier digital nuclear magnetic resonance spectrometer, and the characterization data were the same as in Example 1.
Embodiment 3
[0045] In a 100 mL round bottom flask, 1.5 g methyl benzoate and 1.1 g benzylamine were dissolved in toluene, and 0.3 g g catalyst ZrOCl was added 2 ·8H 2 O and 0.2g citric acid were heated to reflux, and the reaction was terminated when there was no ethyl benzoate detected by TLC. After the reaction mixture, toluene was removed under reduced pressure, 20 mL of ethyl acetate was added, filtered with suction, washed, concentrated, and crystallized to obtain a white solid. The structural formula of the obtained product is as follows:
[0046] The yield was 91.0%.
[0047] The obtained product was characterized by a Bruker Avance type superconducting Fourier digital nuclear magnetic resonance spectrometer, and the characterization data were the same as in Example 1.
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