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A pd (pph 3 ) 4 Catalytic synthesis of amides

A technology of amide compounds and synthesis methods, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid amides, etc., can solve the problems of high toxicity and bad smell of aromatic hydrocarbons, and achieve simple operation and strong atom economy Effect

Inactive Publication Date: 2019-09-24
中国人民解放军63975部队
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, halogenated aromatic hydrocarbons are highly toxic, have an unpleasant odor, and require the addition of several equivalents of POCl 3

Method used

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  • A pd (pph <sub>3</sub> ) <sub>4</sub> Catalytic synthesis of amides
  • A pd (pph <sub>3</sub> ) <sub>4</sub> Catalytic synthesis of amides
  • A pd (pph <sub>3</sub> ) <sub>4</sub> Catalytic synthesis of amides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of N,N-dimethylbenzamide from benzoic acid and DMF:

[0023]

[0024] Add benzoic acid (0.036g, 0.3mmol), Pd(PPh 3 ) 4 (0.017g, 0.015mmol), K 2 S 2 o 8 (0.162g, 0.6mmol), DMF (1.5mL), tighten the bottle cap, and react at an external temperature of 160°C for 18 h; monitor by gas chromatography; =4:1) After separation, a colorless transparent liquid was obtained with a yield of 75%.

[0025] 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

[0027] Synthesis of N,N-dimethyl-2-chlorobenzamide from 2-chlorobenzoic acid and DMF:

[0028]

[0029] Add 2-chlorobenzoic acid (0.047g, 0.3mmol), Pd(PPh 3 ) 4 (0.017g, 0.015mmol), K 2 S 2 o 8 (0.162g, 0.6mmol), DMF (1.5mL), tighten the bottle cap, and react at 160°C for 18h at an external temperature; monitor by gas chromatography; 4:1) was separated to give a white solid in 80% yield.

[0030] 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

[0032] Synthesis of N,N-dimethyl-2-trifluoromethylbenzamide from 2-trifluoromethylbenzoic acid and DMF:

[0033]

[0034] Add 2-trifluoromethylbenzoic acid (0.057g, 0.3mmol), Pd(PPh 3 ) 4 (0.017g, 0.015mmol), K 2 S 2 o 8 (0.162g, 0.6mmol), DMF (1.5mL), tighten the bottle cap, and react at 160°C for 18h at an external temperature; monitor by gas chromatography; 4:1) A white solid was obtained after isolation in 72% yield.

[0035] 1 H NMR (300MHz, CDCl 3 )δ7.70(d, J=7.8Hz, 1H), 7.62(dd, J=5.9, 3.4Hz, 1H), 7.51(t, J=7.7Hz, 1H), 7.35(d, J=7.5Hz, 1H), 3.14(s, 3H), 2.80(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ169.09(s), 135.38(d, J=2.2Hz), 132.33(d, J=0.8Hz), 129.14(s), 127.42(s), 126.70(d, J=4.6Hz), 38.95( s), 34.93(s); MS(70eV, EI) m / z(EI)C 10 h 10 f 3 NO[M]: 217.19, 75(33), 95(37), 145(63), 173(61), 216(100), 217(14).

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Abstract

The invention relates to a Pd(PPh3)4 catalyzed amide compound synthesis method. The synthesis method takes carboxylic acid as the substrate, and adopts N-substituted formamide as the amine source to synthesize an amide compound under the catalysis of Pd(PPh3)4. The method is widely applicable to substrates with different functional groups. The amide compound efficiently constructed by the invention is an important skeleton of many organic molecules, drugs, peptides, bioactive molecules and natural products. 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 Pd(PPh 3 ) 4 Catalytic synthesis of amides. Background technique [0002] The transition metal palladium (Pd) is a very widely used transition metal catalyst, which provides a very rich variety of options for the construction of C-C bonds and C-heteroatom bonds. It can be said that no other transition metal can be like palladium, Participate in the formation of so many types of C-C and C-heteroatom bonds. [0003] The amide bond is an important chemical bond in organic synthesis, which widely exists in organic molecules, bioactive molecules, and drug molecules. Especially in the field of medicine, many drugs contain amide bonds, such as the well-known penicillin and vancomycin. [0004] [0005] The research on amidation reactions using primary and secondary amines as amine sources has become increasingly mature, and the reactions using other nitrogen-containing compounds as amine sources have gradually attract...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/12C07C233/65C07C253/30C07C255/57C07C235/60C07D307/68C07D333/38C07D295/192C07C233/11C07C233/05
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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