Method for synthesizing acetanilide derivatives

A technology of aniline derivatives and synthesis methods, applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as no literature reports, and achieve easy operation, cheap and easy to obtain raw materials, stable and stable. effect of operation

Active Publication Date: 2019-03-12
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there have been no literature reports

Method used

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  • Method for synthesizing acetanilide derivatives
  • Method for synthesizing acetanilide derivatives
  • Method for synthesizing acetanilide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the synthesis of 4-methoxyacetanilide

[0015]

[0016] Add 2mL of acetonitrile, 36.9mg of p-methoxyaniline, 68.4mg of potassium thioacetate, and 6.2mg of tert-butyl nitrite into a 25mL reaction tube, and react with magnetic stirring at 25°C for 4 hours. After the reaction is finished, extract with ethyl acetate, combine the organic phases, evaporate most of the solvents under reduced pressure, use petroleum ether and ethyl acetate as eluent with a composition of 5:1, and conduct column chromatography to separate the remaining mixed solution. After purification, the desired product was obtained as a light yellow solid, 44.6 mg, with a yield of 90%.

[0017] Its NMR data are as follows:

[0018] 1 H NMR (300MHz, CDCl 3 ) δ = 8.24 (s, 1H), 7.39 (d, J = 8.9Hz, 2H), 6.81 (d, J = 8.9Hz, 2H), 3.76 (s, 3H), 2.10 (s, 3H).

Embodiment 2

[0019] Embodiment 2: the synthesis of 4-methylacetanilide

[0020]

[0021] Add 2 mL of acetonitrile, 32.1 mg of p-methylaniline, 68.4 mg of potassium thioacetate, and 6.2 mg of tert-butyl nitrite into a 25 mL reaction tube, and react with magnetic stirring at 25° C. for 4 hours. After the reaction is completed, extract with ethyl acetate, combine the organic phases, evaporate most of the solvents under reduced pressure, use petroleum ether and ethyl acetate as eluent with a composition combination of 10:1, and perform column chromatography on the remaining mixed solution After separation and purification, the desired product was obtained as a light yellow solid, 35.8 mg, with a yield of 80%.

[0022] Its NMR data are as follows:

[0023] 1 H NMR (300MHz, CDCl 3 ) δ = 8.10 (s, 1H), 7.39 (d, J = 7.8Hz, 2H), 7.10 (d, J = 7.5Hz, 2H), 2.31 (s, 3H), 2.13 (s, 3H).

Embodiment 3

[0024] Example 3: Synthesis of 4-fluoroacetanilide

[0025]

[0026] Add 2 mL of acetonitrile, 33.3 mg of p-fluoroaniline, 68.4 mg of potassium thioacetate, and 6.2 mg of tert-butyl nitrite into a 25 mL reaction tube, and react with magnetic stirring at 25° C. for 4 hours. After the reaction is completed, extract with ethyl acetate, combine the organic phases, evaporate most of the solvents under reduced pressure, use petroleum ether and ethyl acetate as eluent with a composition combination of 10:1, and perform column chromatography on the remaining mixed solution After separation and purification, the desired product was obtained as a light yellow solid, 30.3 mg, with a yield of 66%.

[0027] Its NMR data are as follows:

[0028] 1 H NMR (300MHz, CDCl 3 ) δ = 7.90 (s, 1H), 7.48-7.43 (m, 2H), 7.02-6.96 (m, 2H), 2.15 (s, 3H).

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Abstract

The invention discloses a method for synthesizing acetanilide derivatives, and belongs to the technical field of organic synthetic intermediates. The method particularly includes steps of adding aniline derivatives, potassium thioacetate, tert-butyl nitrite and acetonitrile into reaction tubes; tightening plugs of the reaction tubes; carrying out magnetic stirring reaction at the temperature of 25DEG C for 4 hours. The aniline derivatives and the potassium thioacetate which is low in cost and easy to operate, is easily available and is stable are used as acetylation reagents, and accordinglya series of acetanilide derivatives can be efficiently synthesized by the aid of the method under the room-temperature conditions. The acetanilide derivatives which are compounds contain arylamine skeletons and can be used for synthesizing and modifying organic synthetic intermediates and medicines, and novel and effective synthesis processes can be provided to screening medicines. The reaction can be accelerated by the tert-butyl nitrite to synthesize the compounds which are the acetanilide derivatives. Compared with existing synthesis methods, the method has the advantages that reaction conditions are simple, raw materials for the acetanilide derivatives are low in cost and easy to operate, are easily available and are stable, and functional groups of substrates are good in tolerance.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis intermediates, in particular to a method for synthesizing acetanilide derivative compounds. Background technique [0002] Acetanilide derivatives are important fine organic chemical intermediates, widely used in medicine, pesticide, chemical industry and other fields. The traditional synthetic method is mainly the acetylation of aniline, carboxylic acid and its derivatives. Acetylation is the most basic chemical transformation in organic synthesis. It is often used to protect functional groups such as hydroxyl or amino groups, and is widely used in organic synthesis. At present, many acetylation reagents have been reported in the literature, among which the two most commonly used and highly active acetylation reagents are acetyl chloride and acetic anhydride. Although they exhibited good reactivity in the acetylation of aniline with almost quantitative yields, these two reagents were n...

Claims

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Application Information

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IPC IPC(8): C07C233/25C07C233/07C07C233/15C07C231/02
CPCC07C233/07C07C233/15C07C233/25
Inventor 张洁雨柯求敏田飞涛严国兵何平
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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