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A kind of method for preparing amide by arylmethane derivative and nitrile
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A technology of arylmethane and its derivatives, which is applied in the field of organic synthesis, can solve the problems of toxicity, narrow nitrile source, and demand, and achieve the effects of cheap and easy-to-obtain raw materials, mild reaction conditions, and wide applicability
Active Publication Date: 2018-08-17
HUNAN UNIV
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[0004] There are currently five reported methods for the direct synthesis of amides from arylmethane and nitrile compounds, but these methods have narrow nitrile sources and use nitriles as solvents, and use uncommon oxidants, such as ceric ammonium nitrate (CAN) and fluorine Reagents are difficult to handle and the atom economy is not good. Our yield of similar compounds is much higher than theirs
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Synthetic example 1
[0024] Synthesis of N-Benzhydrylacetamide
[0025] Add 0.2mmol diphenylmethane, 0.04mmol manganese acetate dihydrate, 0.4mmol DDQ, 0.5mL acetonitrile, 0.15mL TFA into the reactor, mix, heat to 90°C under nitrogen, keep stirring for 12h, stop the reaction, and cool to room temperature , adding potassiumcarbonate to neutrality, extracting with ethyl acetate, drying, and distilling off the solvent under reduced pressure. The crude product was separated by column chromatography to obtain the target product with a yield of 90%. 1 H NMR (400MHz, CDCl 3 ): δ7.34-7.26(m,6H),7.24-7.21(m,4H),6.24(d,J=8.0Hz,1H),6.09(d,J=6.2Hz,1H),2.06(s, 3H).
[0028] Add 0.2mmol ethylbenzene, 0.04mmol manganese acetate dihydrate, 0.4mmol DDQ, 0.5mL acetonitrile, 0.15mL TFA to the reactor, mix, heat to 90°C under nitrogen, keep stirring for 12h, stop the reaction, cool to room temperature, Add potassiumcarbonate until neutral, extract with ethyl acetate, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product with a yield of 59%. 1 H NMR (400MHz, CDCl 3 ): δ7.27-7.18 (m, 5H), 5.83 (s, 1H), 5.07–4.99 (m, 1H), 1.89 (s, 3H), 1.40 (d, J=6.9Hz, 1H).
Synthetic example 3
[0030] Synthesis of N-(2-methyl-1-phenylpropyl)acetamide
[0031] Add 0.2mmol isobutylbenzene, 0.04mmol manganese acetate dihydrate, 0.4mmol DDQ, 0.5mL acetonitrile, 0.15mL TFA into the reactor, mix, heat to 90°C under nitrogen, keep stirring for 12h, stop the reaction, and cool to room temperature , adding potassiumcarbonate to neutrality, extracting with ethyl acetate, drying, and distilling off the solvent under reduced pressure. The crude product was separated by column chromatography to obtain the target product with a yield of 20%. 1 H NMR (400MHz, CDCl 3 ): δ7.25(d, J=7.6Hz, 1H), 7.19-7.14(m, 4H), 7.16(d, J=8.3Hz, 2H), 5.67(d, J=7.4Hz, 1H), 4.69 (t,J=8.5Hz,1H),2.00-1.95(m,1H),1.93(s,3H),0.90(d,J=6.7Hz,3H),0.76(d,J=6.7Hz,3H) .
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Abstract
The invention provides a simple and efficient method for directly preparing an amide compound from an arylmethane derivative and nitrile. In the method, manganese triacetate dihydrate is used as a catalyst, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) is used as an oxidizing agent. The method has the characteristics that raw materials are cheap and easy to obtain, the source of the nitrile is wide, reaction conditions are mild, the applicability is wide and the like. The method solves the problems that ceric ammonium nitrate (CAN) and a fluorine agent which are used by a method for directly synthesizing amide by using arylmethane and nitrile compounds are hard to treat, atomic economy is poor, the source of the nitrile is narrow and the like.
Description
【Technical field】 [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing amides from arylmethane derivatives and nitriles. 【Background technique】 [0002] Amides are important raw materials and intermediates in organic synthesis, and have attracted a lot of interest in industry and academia in recent years. It can form peptide bonds in proteins such as enzymes, and has high utilization value in biology and pesticides, and also shows good biomedical activity in the field of medicine. Amide compounds not only have excellent biological activity but also have variable chemical structures. They are one of the hotspots in the research of organic synthesis and medicinal chemistry. The exploration of the synthetic routes of these compounds is also constantly in-depth. [0003] The reaction of carboxylic acid or acid chloride or acid anhydride compound with amine to generate amide compound is a widely used synthetic method. Some peop...
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