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Method for synthesizing phosphorus-oxychloride-promoted amide compound

A technology of amide compounds and amide compounds, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of carboxylic acid amides, can solve the problems of high price, long reaction time, environmental pollution, etc. Yield, effect of widely applicable preparation method

Inactive Publication Date: 2016-12-07
中国人民解放军63975部队
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The most widely studied synthesis method for amide bonds is the metal-catalyzed C-C or C-N coupling reaction. During the reaction, metal catalysts, oxidants, etc. need to be added, the reaction conditions are relatively high, the reaction time is relatively long, and some transitions Metal catalysts are expensive, and a large amount of oxidant needs to be added in the reaction process, which will inevitably lead to an increase in synthesis cost and environmental pollution. Therefore, the development of convenient, fast and efficient synthesis methods is still a research hotspot in the current amide bond synthesis method

Method used

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  • Method for synthesizing phosphorus-oxychloride-promoted amide compound
  • Method for synthesizing phosphorus-oxychloride-promoted amide compound
  • Method for synthesizing phosphorus-oxychloride-promoted amide compound

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0031] Synthesis of N,N-dimethylbenzamide from benzoic acid and DMF:

[0032]

[0033] Add benzoic acid (0.036g, 0.3mmol), POCl 3 (lequiv), DMF (2mL), screw the bottle cap tightly, and react in an airtight manner at an external temperature of 120°C for 1 hour; monitor the completion of the reaction by gas chromatography; after the reaction liquid is cooled, add 10 mL of saturated Na 2 CO 3 The aqueous solution was extracted with ethyl acetate (3×10 mL), the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and a colorless and transparent Liquid, 90% yield.

[0034] 1 H NMR (300MHz, CDCl 3 )δ7.39(s, 5H), 3.10(s, 3H), 2.96(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ171.76, 136.34, 129.61, 128.43, 127.11, 39.69, 35.43; MS (70eV, EI) m / z (EI) C 9 h 11 NO[M]: 149.19, 51(36), 77(100), 105(29), 148(56), 149(5).

example 2

[0036] Synthesis of N,N-dimethyl-3-methylbenzamide from 3-methylbenzoic acid and DMF:

[0037]

[0038] Add 3-methylbenzoic acid (0.041g, 0.3mmol), POCl3 (lequiv), DMF (2mL), screw the bottle cap tightly, and react in an airtight manner at an external temperature of 120°C for 1 hour; monitor the completion of the reaction by gas chromatography; after the reaction liquid is cooled, add 10 mL of saturated Na 2 CO 3 The aqueous solution was extracted with ethyl acetate (3×10 mL), the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and a colorless and transparent Liquid, 95% yield.

[0039] 1 H NMR (300MHz, CDCl 3 )δ7.23(dq, J=13.0, 7.4Hz, 4H), 3.04(d, J=39.5Hz, 6H), 2.37(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ171.94, 138.28, 136.37, 130.28, 128.24, 127.73, 124.05, 39.68, 35.38, 21.45; MS (70eV, EI) m / z (EI) C 10 h 13 NO[M]: 163.22, 65(27), 91(100), 119(33), 162(28), 163(4).

example 3

[0041] Synthesis of N,N-dimethyl 4-hydroxybenzamide from 4-hydroxybenzoic acid and DMF:

[0042]

[0043] Add 4-hydroxybenzoic acid (0.041g, 0.3mmol), POCl 3 (lequiv), DMF (2mL), screw the bottle cap tightly, and react in an airtight manner at an external temperature of 120°C for 1 hour; monitor the completion of the reaction by gas chromatography; after the reaction liquid is cooled, add 10 mL of saturated Na 2 CO 3 The aqueous solution was extracted with ethyl acetate (3×10 mL), the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and a colorless and transparent Liquid, 55% yield.

[0044] 1 H NMR (300MHz, CDCl 3 )δ7.25-7.19 (m, 2H), 6.74-6.66 (m, 2H), 3.06 (d, J=19.0Hz, 6H); 13 C NMR (75MHz, CDCl 3 )δ172.82, 158.77, 129.20, 126.31, 115.50, 38.04 (d, J=321.6Hz); MS (70eV, EI) m / z (EI) C 9 h 11 NO 2 [M]: 165.19, 63(26), 65(100), 73(44), 93(83), 121(82), 164(28), 165(3).

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Abstract

The invention relates to a method for synthesizing a phosphorus-oxychloride-promoted amide compound. The synthesizing method includes the steps that carboxylic acid serves as one reactant, another reactant (N,N-dialkyl methanamide) serves as a solvent, one equivalent of phosphorus oxychloride is added, and the amide compound is prepared. The reaction substrates are low in price and easy to get, the nature is stable, toxicity is small, the reaction speed is high, conditions are moderate, and the reaction substrates can be widely applied to substrates with different functional groups. The efficiently-constructed amide compound is an important molecular skeleton for many medicines, bioactive molecules and natural products, and the synthesizing method is a widely-applicable preparing method for synthesizing the compound.

Description

technical field [0001] The invention relates to a method for synthesizing amide compounds promoted by phosphorus oxychloride. Background technique [0002] The amide bond is one of the most important functional groups in organic chemistry, and it is also the most basic structural unit of some drugs with important biological activities such as anti-tumor and anti-virus. Therefore, the breakthrough in the synthesis of amide bonds is not only in the field of chemistry, It is of great significance in the fields of biology and medicinal chemistry. The most widely studied synthesis method for amide bonds is the metal-catalyzed C-C or C-N coupling reaction. During the reaction, metal catalysts, oxidants, etc. need to be added, the reaction conditions are relatively high, the reaction time is relatively long, and some transitions Metal catalysts are expensive, and a large amount of oxidant needs to be added in the reaction process, which will inevitably lead to an increase in synth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/14C07C233/65C07C235/46C07C237/30C07C253/30C07C255/57C07D213/81C07D213/82C07D295/192C07C233/11C07C233/05
CPCC07C231/14C07C253/30C07D213/81C07D213/82C07D295/192C07C233/65C07C235/46C07C237/30C07C233/11C07C233/05C07C255/57
Inventor 肖军华毕晓静李宇刘瑛王红梅李君臣
Owner 中国人民解放军63975部队
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