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FeCl3 catalyzed amide compound synthesis method

A technology for amide compounds and synthesis methods, applied in chemical instruments and methods, preparation of organic compounds, formation/introduction of amide groups, etc., can solve the problems of lack of environmental protection and economy, high toxicity, high odor, etc. Atomic economy, low toxicity, stable properties

Inactive Publication Date: 2017-11-24
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

In the amidation reaction catalyzed by palladium in the literature, the substrates used are mostly halogenated aromatic hydrocarbons, which are highly toxic, smelly, and expensive. During the reaction process, ligands and 2 to 3 equivalents of phosphorus oxychloride need to be added, and in the relative It is carried out at a higher reaction temperature, which is lacking in terms of environmental protection and economy

Method used

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  • FeCl3 catalyzed amide compound synthesis method
  • FeCl3 catalyzed amide compound synthesis method
  • FeCl3 catalyzed amide compound synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of N,N-dimethylbenzamide from benzoic acid and DMF:

[0022]

[0023] Add benzoic acid (0.036g, 0.3mmol), FeCl 3 (0.0049g, 0.03mmol), TBHP (0.116g, 0.9mmol, 70% aqueous solution), DMF (1mL), toluene (1mL), pyridine (0.118g, 1.5mmol), fill it with argon, tighten the bottle cap , external temperature 85 ℃ airtight reaction 8h; gas chromatography monitoring; after the reaction was completed, the solvent was removed by rotary evaporation, and a colorless transparent liquid was obtained after separation by column chromatography (ethyl acetate:petroleum ether=4:1), with a yield of 89% .

[0024] 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(s), 136.34(s), 129.61(s), 128.43(s), 127.11(s), 39.69(s), 35.43(s); MS(70eV, EI) m / z(EI) C 9 h 11 NO[M]: 149.19, 51(36), 77(100), 105(29), 148(56), 149(5).

Embodiment 2

[0026] Synthesis of N,N-dimethyl-2-chlorobenzamide from 2-chlorobenzoic acid and DMF:

[0027]

[0028] Add 2-chlorobenzoic acid (0.047g, 0.3mmol), FeCl 3 (0.0049g, 0.03mmol), TBHP (0.116g, 0.9mmol, 70% aqueous solution), DMF (1mL), toluene (1mL), pyridine (0.118g, 1.5mmol), fill it with argon, tighten the bottle cap , closed reaction at an external temperature of 85° C. for 8 h; gas chromatography monitoring; after the reaction was completed, the solvent was removed by rotary evaporation, and a white solid was obtained after separation by column chromatography (ethyl acetate:petroleum ether=4:1), with a yield of 92%.

[0029] 1 H NMR (300MHz, CDCl 3 )δ7.35-7.19 (m, 4H), 3.07 (s, 3H), 2.80 (s, 3H); 13 C NMR (75MHz, CDCl 3 )δ168.57(s), 136.43(s), 130.28(d, J=14.4Hz), 129.67(s), 127.85(s), 127.29(s), 38.18(s), 34.76(s); MS( 70eV, EI)m / z(EI)C 9 h 10 ClNO [M]: 183.63, 75(100), 111(84), 139(59), 182(16), 184(6).

Embodiment 3

[0031] Synthesis of N,N-dimethyl-2-iodobenzamide from 2-iodobenzoic acid and DMF:

[0032]

[0033] Add 2-iodobenzoic acid (0.074g, 0.3mmol), FeCl 3 (0.0049g, 0.03mmol), TBHP (0.116g, 0.9mmol, 70% aqueous solution), DMF (1mL), toluene (1mL), pyridine (0.118g, 1.5mmol), fill it with argon, tighten the bottle cap , closed reaction at an external temperature of 85° C. for 8 h; gas chromatography monitoring; after the reaction was completed, the solvent was removed by rotary evaporation, and a light yellow solid was obtained after separation by column chromatography (ethyl acetate:petroleum ether=4:1), with a yield of 95%.

[0034] 1 H NMR (300MHz, CDCl 3 )δ7.81(dd, J=8.0, 0.8Hz, 1H), 7.38(td, J=7.5, 1.1Hz, 1H), 7.21(dd, J=7.6, 1.6Hz, 1H), 7.09-7.03(m , 1H), 3.13(s, 3H), 2.84(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ170.8, 142.9, 139.1, 130.2, 128.5, 127.1, 92.5, 38.5, 34.8; MS (70eV, EI) m / z (EI) C 9 h 10 INO, [M]: 275.09, 50(100), 76(91), 91(14), 148(11), 231(5), 274(20), 275...

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Abstract

The invention relates to an FeCl3 catalyzed amide compound synthesis method. According to the synthesis method, carboxylic acid and N-substituted formamide are employed to synthesize an amide compound under the catalysis of FeCl3. The synthesis method provided by the invention has the characteristics of mild conditions, high reaction efficiency, and wide applicability to substrates of different functional groups. The amide compound efficiently constructed by the invention is an important skeleton of many organic molecules, drugs, proteins and bioactive molecules. The synthesis method provided by the invention provides a widely applicable preparation method for synthesis of the compounds.

Description

technical field [0001] The present invention relates to a kind of FeCl 3 Catalytic synthesis of amides. Background technique [0002] Transition metal-catalyzed organic reactions are effective strategies for building chemical bonds. Affected by early research reports and the performance of the catalyst itself, many reactions are limited to the use of rare and non-renewable transition metal elements such as ruthenium, rhodium, and palladium, which are expensive and highly toxic, and are not suitable for large-scale application. Iron (Fe) is the most abundant transition metal resource on the earth. Although it has d orbital electrons like ruthenium, rhodium, and palladium, there are few studies on it as a catalyst. Studies have shown that iron has low catalytic efficiency or almost no catalytic activity in many reactions, but as a "green" metal catalyst with low price and low toxicity, iron catalyst is undoubtedly the best choice among transition metal catalysts. [0003] I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/06C07C231/10C07C233/65C07C233/11C07C233/05C07C235/60C07D213/81C07D295/192C07D307/68C07D333/38
CPCC07B43/06C07C231/10C07D213/81C07D295/192C07D307/68C07D333/38C07C233/65C07C233/11C07C233/05C07C235/60
Inventor 肖军华毕晓静李君臣王红梅孟凡华
Owner 中国人民解放军63975部队
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