Environmental-friendly nitrile hydrolysis method

A green, alkaline catalyst technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of large amount of catalyst, poor catalyst effect, high toxicity and so on

Inactive Publication Date: 2013-08-07
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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  • Environmental-friendly nitrile hydrolysis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of benzamide from benzonitrile

[0020]

[0021] Add CsOH·H to the reaction tube sequentially 2 O (0.0168g, 10mol%), PhCN (1.0mmol) and H 2 O (0.04mL, 2.2equiv.), then add DMSO (0.5mL) as solvent, seal the reaction tube and heat to 60oC for 12h. 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 94%. 1 HNMR (500MHz, d 6 -DMSO): δ8.01(b,1H),7.88-7.86(m,2H),7.54-7.51(m,1H),7.47-7.44(m,2H),7.39(b,1H). 13 CNMR (125.4MHz, d 6 -DMSO): δ168.0, 134.1, 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

[0023] Preparation of p-toluamide from p-methylbenzonitrile

[0024]

[0025] Add CsOH·H to the reaction tube sequentially 2 O (0.0168g, 10mol%), p-tolunitrile (1.0mmol) and H 2 O (0.04mL, 2.2equiv.), then add DMSO (0.5mL) as solvent, seal the reaction tube and heat to 60oC for 24h. The reaction conversion rate was over 91% as measured by GC-MS, and the product was separated and purified by column chromatography with a separation yield of 85%. 1 HNMR (500MHz, d 6 -DMSO):δ7.71(d,J=8.0Hz,2H),7.25(m,3H),6.08(b,1H),5.93(b,1H),2.40(s,3H). 13 CNMR (125.4MHz, d 6 -DMSO): δ169.6, 142.6, 130.6, 129.4, 127.5, 21.6. 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

[0027] Preparation of m-methylbenzamide from m-methylbenzonitrile

[0028]

[0029] Add CsOH·H to the reaction tube sequentially 2 O (0.0168g, 10mol%), m-tolunitrile (1.0mmol) and H 2 O (0.04mL, 2.2equiv.), then add DMSO (0.5mL) as solvent, seal the reaction tube and heat to 60oC for 24h. 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 85%. 1 HNMR (500MHz, d 6 -DMSO): δ7.65(s,1H),7.59(s,1H),7.34(s,1H),7.27(s,1H),6.15(b,2H),2.40(s,3H). 13 CNMR (125.4MHz, d 6 -DMSO): δ169.8, 138.5, 133.4, 132.7, 128.5, 128.1, 124.3, 21.3. 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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PUM

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Abstract

The invention provides an environmental-friendly nitrile hydrolysis method. The hydrolysis reaction of a nitrile compound is catalyzed by using a base catalyst in an air condition, wherein the reaction temperature is from room temperature to 120 DEG C and the reaction time is 1-48 hours. According to the method, a nontransition metal catalyst which is low in price and small in toxicity is used, the nitrile is hydrolyzed directly in the air condition to obtain the first-grade amide. The reaction is mild in condition, easy to operate, and does not cause over-hydrolysis of the nitrile to reduce the yield rate of the target product amide, and therefore the product separation and purification are simple and easy, and high in recycling rate. The method is quite low in requirements for reaction condition and has good research and industrial application prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a green method for preparing primary amides by gentle and efficient hydrolysis of nitrile compounds, that is, a green hydrolysis method for 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 hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/65C07C231/06C07C233/58C07C233/05C07C233/11C07C237/30C07D213/81C07D213/82C07D241/24C07D333/38
Inventor 徐清陈浩楠戴武杰陈逸林佐强
Owner WENZHOU UNIVERSITY
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