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Method for catalytic preparation of amide and derivatives thereof in aqueous phase

A technology for derivatives and compound amides, applied in the field of preparing amides and derivatives thereof

Inactive Publication Date: 2010-11-24
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In pure aqueous phase, with CuI / NH 3 ·H 2 O is a catalyst, and the method of catalyzing the hydrolysis of nitriles to synthesize amides and derivatives thereof has not been reported so far

Method used

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  • Method for catalytic preparation of amide and derivatives thereof in aqueous phase
  • Method for catalytic preparation of amide and derivatives thereof in aqueous phase
  • Method for catalytic preparation of amide and derivatives thereof in aqueous phase

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of benzamide

[0024] In the reaction vessel, add cuprous iodide 0.05mmol (9.5mg), 25%-28% ammoniacal liquor 6.8mg, water 2mL, stir at room temperature for 15 minutes, then add benzonitrile 0.5mmol (51.6mg), at 100 It was reacted in an oil bath at ℃ for 21 hours, cooled to room temperature, the reaction mixture was extracted with ethyl acetate, the organic layer was concentrated under reduced pressure, and purified by column chromatography to obtain a white solid product with a yield of 97%. 1 H NMR (400MHz, CDCl 3 ): 7.85 (d, 2H, J = 7.2Hz), 7.55 (t, 1H, J = 7.3Hz), 7.46 (m, 2H), 6.33 (br.s, 2H) ppm. (eg figure 1 ) 13 C NMR (100MHz, CDCl 3 ): δ169.7, 133.4, 132.0, 128.6, 127.4ppm. (such as figure 2 ) MS (EI, m / z): 121 [M + ].

Embodiment 2

[0025] Embodiment 2: the preparation of p-nitrobenzamide

[0026] The preparation method was the same as in Example 1, except that 0.5 mmol (74.0 mg) of p-nitrobenzonitrile was added to obtain a light yellow solid product with a yield of 51%. 1 H NMR (400MHz, DMSO-d 6 ): δ8.39-8.23 (m, 3H), 8.09 (d, 2H, J=8.8Hz), 7.75 (br.s, 1H) ppm. 13 C NMR (100MHz, DMSO-d 6 ): δ166.4, 149.3, 140.2, 129.1, 123.7ppm. MS (EI, m / z): 166 [M + ].

Embodiment 3

[0027] Embodiment 3: the preparation of p-bromobenzamide

[0028] The preparation method was the same as in Example 1, except that 0.5 mmol (91.0 mg) of p-bromobenzonitrile was added to obtain a white solid product with a yield of 87%. 1 H NMR (400MHz, DMSO-d 6 ): δ8.01 (br.s, 1H), 7.78 (d, 2H, J=8.5Hz), 7.64 (d, 2H, J=8.5Hz), 7.42 (br.s, 1H) ppm. 13C NMR (100MHz, DMSO-d 6 ): δ166.5, 133.0, 130.8, 129.2, 124.6ppm.MS (EI, m / z): 200[M + ].

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Abstract

The invention discloses a method for catalytic preparation of amide and derivatives thereof in an aqueous phase. A water soluble coordination compound is taken as a catalyst and efficiently catalyzes amidation of nitrile in the aqueous phase to prepare amide derivatives. The invention provides a novel method for efficiently preparing the amide derivatives, which has the advantages of environmental friendliness, simple and convenient operation, safety and low price. Compared with the prior art, the method is suitable for lots of functional groups, and also has the advantages of simple operation, high yield, easy separation and purification, safety, low price and small pollution.

Description

1. Technical field [0001] The invention relates to a method for preparing amides and derivatives thereof through amidation of nitriles catalyzed by coordination compounds in pure water phase. 2. Background technology [0002] Amides not only have very important industrial application value, such as widely used in the production of engineering plastics, detergents, lubricants; but also important organic synthesis intermediates, used in the synthesis and production of drugs. The synthesis method of amides and derivatives thereof has always been a research focus (see: (a) C.E.Mabermann in Encyclopedia of Chemical Technology, Vol.1 (Ed.: J.I.Kroschwitz), Wiley, New York, 1991, p.251-266; (b) D.Lipp in Encyclopedia of Chemical Technology, Vol.1 (Ed.: J.I.Kroschwitz), Wiley, New York, 1991, p.266-287; (c) R.Opsahl in Encyclopedia of Chemical Technology, Vol.2 ( Ed.: J.I. Kroschwitz), Wiley, New York, 1991, p.346-356.). The traditional methods of synthesizing amides include: cond...

Claims

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Application Information

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IPC IPC(8): C07C231/06C07C233/65C07C235/46C07C235/84C07D213/82C07C233/11C07C233/05C07C233/09
Inventor 周向葛李正凯王利霞
Owner SICHUAN UNIV
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