Acetanilide compound and preparation method and application thereof
A technology of acetanilide and compounds, applied in the field of organic synthesis, can solve the problems of adding noble metal catalysts, cumbersome synthesis steps, long reaction time, etc., and achieve the effect of non-toxic raw materials, simple synthesis steps, and good inhibitory effect
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Embodiment 1
[0054] In the reactor, add 0.5 mmol aniline and 5 mmol 1,4-dioxane, 0.25 mmol di-tert-butyl peroxide, 0.05 mmol trifluoroacetic acid, and stir the reaction at 80°C for 16 hours, After the reaction, cool to room temperature, dilute the reaction solution, filter, and remove the solvent by rotary evaporation under reduced pressure to obtain the crude product, which is purified by column chromatography to obtain 2-(2-hydroxyethoxy)-N-phenylacetamide compound 2a.
[0055] The hydrogen spectrogram and the carbon spectrogram of gained product 2a are respectively as follows figure 1 and figure 2As shown, the structural characterization data are as follows:
[0056] 1 H NMR (400MHz, CDCl 3 )δ8.83(s,1H),7.59(d,J=8.0Hz,2H),7.31(t,J=7.8Hz,2H),7.11(t,J=7.4Hz,1H),4.10(s, 2H),3.87–3.83(m,2H),3.72–3.69(m,2H);
[0057] 13 C NMR (101MHz, CDCl 3 )δ168.23, 137.30, 128.98, 124.55, 119.95, 73.17, 70.54, 61.48;
[0058] HRMS(ESI): Calcd.for C 10 h 14 NO 3 [M+H] + :196.0968; found: 196.0...
Embodiment 2
[0062] In the reactor, add 0.5 mmol 4-methylaniline and 10 mmol 1,4-dioxane, 1 mmol hydrogen peroxide, 0.05 mmol m-chloroperoxybenzoic acid, and stir the reaction at 100°C After 16 hours, cool to room temperature after the reaction, dilute the reaction solution, filter, and remove the solvent by rotary evaporation under reduced pressure to obtain the crude product, which is purified by column chromatography to obtain 2-(2-hydroxyethoxy)-N-(p-tolyl ) acetamide compound 2b.
[0063] The hydrogen spectrogram and the carbon spectrogram of gained product 2b are respectively as follows image 3 and Figure 4 As shown, the structural characterization data are as follows:
[0064] 1 H NMR (400MHz, CDCl 3 )δ8.67(s,1H),7.38(d,J=8.3Hz,2H),7.03(d,J=8.2Hz,2H),4.02(s,2H),3.79–3.73(m,2H), 3.64–3.60(m,2H),2.23(s,3H);
[0065] 13 C NMR (101MHz, CDCl 3 )δ168.04, 134.73, 134.16, 129.46, 119.98, 73.16, 70.55, 61.48, 20.87;
[0066] HRMS(ESI): Calcd.for C 11 h 16 NO 3 [M+H] + :210.112...
Embodiment 3
[0070] In the reactor, add 0.5 mmol 3-methoxyaniline and 10 mmol 1,4-dioxane, 0.5 mmol peracetic acid, 0.5 mmol trifluoromethanesulfonic acid, and stir the reaction at 160°C After 16 hours, cool to room temperature after the reaction, dilute the reaction solution, filter, and remove the solvent by rotary evaporation under reduced pressure to obtain the crude product, which is purified by column chromatography to obtain 2-(2-hydroxyethoxy)-N-(3-methoxyphenyl ) acetamide compound 2c.
[0071] The hydrogen spectrogram and the carbon spectrogram of gained product 2c are respectively as follows Figure 5 and Figure 6 As shown, the structural characterization data are as follows:
[0072] 1 H NMR (400MHz, CDCl 3 )δ8.78(s,1H),7.33(s,1H),7.20(t,J=8.1Hz,1H),7.08(d,J=7.9Hz,1H),6.67(d,J=8.2Hz, 1H),4.10(s,2H),3.88–3.83(m,2H),3.79(s,3H),3.73–3.70(m,2H).
[0073] 13 C NMR (101MHz, CDCl 3 )δ168.19, 160.12, 138.52, 129.67, 112.13, 110.29, 105.71, 73.18, 70.56, 61.51, 55.32.
[0074]...
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