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Preparation method of amide from nitrile

An amide and catalyst catalyzing nitrile technology, which is applied in the formation/introduction of amide groups, the preparation of carboxylic acid amides, chemical instruments and methods, etc., can solve the problems of high toxicity, poor catalyst effect, and large amount of catalyst.

Inactive Publication Date: 2013-01-09
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are also many reports on reactions catalyzed by cheap metals, but due to the poor effect of these catalysts, complex ligands are often required, and the amount of catalysts is large, and some cheap metals are also highly toxic.

Method used

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  • Preparation method of amide from nitrile
  • Preparation method of amide from nitrile
  • Preparation method of amide from nitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of benzamide from benzonitrile

[0018]

[0019] Add CsOH·H to the reaction tube sequentially 2 O (0.0336g, 10mol%) and PhCN (2mmol), and ammonia water (1.0mL) was added as a solvent, and the reaction tube was sealed and heated to 100°C for 1h. The reaction conversion rate was over 99% as measured by GC-MS, and the product was separated and purified by column chromatography with a separation yield of 81%. 1 H NMR (500MHz, d 6 -DMSO): δ7.98(b,1H),7.89-7.86(m,2H),7.54-7.51(m,1H),7.47-7.44(m,2H),7.36(b,1H). 13 C NMR (125.4MHz, d 6 -DMSO): δ167.9, 134.2, 131.2, 128.2, 127.4. MS (EI): m / z (%) 224 (6), 223 (32), 222 (14), 132 (2), 131 (8), 130(4),118(2),106(23),105(100),104(5),103(9),91(5),79(9),78(4),77(11), 65(3).

Embodiment 2

[0021] Preparation of p-toluamide from p-methylbenzonitrile

[0022]

[0023] Add CsOH·H to the reaction tube sequentially 2 O (0.0336g, 10mol%) and p-tolunitrile (2mmol), and ammonia water (1.0mL) was added as a solvent, and the reaction tube was sealed and heated to 100°C for 6h. The reaction conversion rate was over 99% as measured by GC-MS, and the product was separated and purified by column chromatography with a separation yield of 80%. 1 H NMR (500MHz, CDCl 3 ):δ7.71(d,J=8.0Hz,2H),7.25(d,J=8.0Hz,2H),6.01(b,2H),2.40(s,3H). 13 C NMR (125.4MHz, CDCl 3 ):δ169.4,142.5,130.6,129.3,127.4,21.5.MS(EI):m / z(%)136(5),135(60),120(8),119(100),117(3), 92(5),91(74),90(8),89(10),65(33),64(4),63(13),51(9),50(6),44(12), 41(5), 40(9), 39(20), 38(4).

Embodiment 3

[0025] Preparation of m-methylbenzamide from m-methylbenzonitrile

[0026]

[0027] Add CsOH·H to the reaction tube sequentially 2 O (0.0336g, 10mol%) and m-tolunitrile (2mmol), and ammonia water (1.0mL) was added as a solvent, and the reaction tube was sealed and heated to 100°C for 6h. The reaction conversion rate was over 99% as measured by GC-MS, and the product was separated and purified by column chromatography with a separation yield of 68%. 1 H NMR (500MHz, d 6 -DMSO): δ7.91(b,1H),7.71(s,1H),7.68-7.66(m,1H),7.33(d,J=5.0Hz,2H),7.30(b,1H),2.35( s,3H). 13 C NMR (125.4MHz, d 6 -DMSO): δ168.0, 137.4, 134.3, 131.7, 128.0, 124.5, 20.9. MS (EI): m / z (%) 136 (6), 135 (63), 120 (9), 119 (100), 117 (4),116(2),92(6),91(77),90(5),89(7),65(18),63(6),62(2),51(4),44 (3), 39(6).

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Abstract

The invention discloses a preparation method of amide from nitrile. The method includes reaction of hydrolysis by heating nitrile under air or nitrogen condition and in ammonia water by alkaline catalyst. The method can implement simple, mild and green hydrolysis and synthesize a series of amide compounds. The catalyst is low in price, small in toxicity, low in dosage, mild in reaction condition and easy to operate in air. Organic solvent is not required in reaction, and ammonia water which is cheap and easy to obtain is used as green solvent. Pollution possibly caused by organic solvent to environment, excess hydrolysis caused by using excess alkali and the like can be reduced greatly.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing amides by hydrolysis of nitriles. Background technique [0002] Amide compounds are not only important organic synthesis reagents, but also widely used intermediates in many fields such as drug synthesis and material research and development. Functionalized amide compounds containing substituents can also exhibit various activities such as pharmacology and biochemistry. Therefore, amides Compounds have a wide range of applications in synthetic application research and industrial medicine. Therefore, the research on the synthesis method of amides has always been one of the interests of people's research. Compared with other methods, the hydrolysis of nitrile compounds is a direct, economical, and facile method to prepare amides. So far, many nitrile hydrolysis methods have been reported in the literature, but there are still their own shortcomings. [00...

Claims

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Application Information

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IPC IPC(8): C07B43/06C07C231/06C07C233/65C07C237/30C07C235/46C07D213/81C07D213/82C07D241/24C07D333/38C07C233/58C07C233/05C07C233/11
Inventor 徐清陈浩楠
Owner WENZHOU UNIVERSITY
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