Para-functionalized arylamine compound and synthesis method thereof
A synthesis method and compound technology, applied in the field of organic chemical synthesis, can solve problems such as complex conditions, and achieve the effects of easy preparation, excellent yield and wide range of substrates
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Embodiment 1
[0069] Example 1, N-(4-hydroxyphenyl)benzamide
[0070]
[0071] In a 20mL reaction tube, add N-hydroxy-N-phenylbenzamide (0.2mmol, 43mg), acetone (2mL) and water (1mL), then add triethylamine (0.4mmol), cool to 0 ℃ , slowly add sulfonyl fluoride imidazolium salt (0.24mmol) while stirring at 0 ℃, after adding, stir for 5 minutes, follow the reaction progress by TLC, after the reaction is completed, the reaction mixture is extracted, and the solvent is removed by rotary evaporation , the crude product was subjected to column chromatography (eluent: petroleum ether: ethyl acetate = 5:1) to obtain pure N-(4-hydroxyphenyl)benzamide in the form of white powder with a yield of 96%.
[0072] 1 H NMR (500MHz, DMSO-d 6 ): δ 10.04 (s, 1H), 9.27 (s, 1H), 7.95–7.93 (m, 2H), 7.58–7.49 (m, 5H), 6.77–6.74 (m, 2H).
[0073] 13 C NMR (126MHz, DMSO-d 6 ): δ165.0, 153.7, 135.2, 131.3, 130.7, 128.3, 127.5, 122.3, 115.0.
Embodiment 2
[0074] Example 2, N-(2-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxyphenyl)benzamide
[0075]
[0076] In a 20 mL reaction tube, add N-(2-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)-N-hydroxybenzamide (0.2 mmol, 96 mg) and acetone ( 2mL) and water (1mL), then add triethylamine (0.4mmol), after cooling to 0°C, add sulfonyl fluorimidazolium salt (0.24mmol) dropwise with stirring at 0°C, after the dropwise addition is complete, stir for five After the reaction was completed, the reaction mixture was extracted, and the solvent was removed by rotary evaporation. The crude product was subjected to column chromatography (eluent: petroleum ether: ethyl acetate = 5:1) to obtain a white powder. Pure N-(2-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxyphenyl)benzamide, the yield is 70%.
[0077] 1 H NMR (500MHz, CDCl 3 ): δ9.34(s, 1H), 7.91(dd, J=14.3, 8.2Hz, 3H), 7.62(d, J=7.0Hz, 4H), 7.52(t, J=7.4Hz, 1H), 7.41 (dt, J=14.8, 7.5Hz, 4H), 7.34(t, J=7.4Hz, 4H), 7.28(s, 1H), 6.7...
Embodiment 3
[0079] Example 3, N-(2-methyl-4-(2,2,2-trifluoroethoxy)phenyl)benzamide
[0080]
[0081] In a 20mL reaction tube, add N-hydroxy-N-(o-tolyl)benzamide (0.2mmol, 45mg) and trifluoroethanol (1mL), then add potassium carbonate (0.4mmol), cool to -40°C , add sulfonyl fluoride imidazolium salt while stirring at -40 ℃, after completion, stir for five minutes, follow the reaction progress by TLC, after the reaction is completed, the solvent is removed from the reaction mixture by rotary evaporation, and the crude product is subjected to column chromatography ( The eluent is petroleum ether:ethyl acetate=5:1) to obtain pure N-(2-methyl-4-(2,2,2-trifluoroethoxy)phenyl)benzamide as white powder , the yield is 84%.
[0082] 1 H NMR (500MHz, CDCl 3 ):δ7.87(d,J=7.4Hz,2H),7.71(d,J=8.6Hz,1H),7.66(s,1H),7.56(t,J=7.4Hz,1H),7.48(t , J=7.6Hz, 2H), 6.84(d, J=2.7Hz, 1H), 6.80(dd, J=8.7, 2.8Hz, 1H), 4.34(q, J=8.1Hz, 2H), 2.30(s , 3H).
[0083] 13 C NMR (126MHz, CDCl 3 ):δ166.0,155.1,134.8...
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