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Preparation method for 5-(N, N-dibenzylamino)acetylsalicylamide

A technology of acetyl salicylamide and chloroacetyl salicylamide, which is applied to the preparation of carboxylic acid amides, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of high cost and low yield, and achieve low production cost, The effect of high yield and large operation pollution

Inactive Publication Date: 2015-04-15
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Aiming at the above-mentioned technical problems in the prior art, the invention provides a kind of 5-(N,N-dibenzylamino) acetyl salicylamide preparation method, described this 5-(N,N-dibenzyl The preparation method of amino) acetylsalicylic amide solves the high cost of the preparation method in the prior art, and the technical problem that the yield is low

Method used

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  • Preparation method for 5-(N, N-dibenzylamino)acetylsalicylamide
  • Preparation method for 5-(N, N-dibenzylamino)acetylsalicylamide
  • Preparation method for 5-(N, N-dibenzylamino)acetylsalicylamide

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Embodiment 1

[0026] A simple and efficient method for preparing 5-(N,N-dibenzylamino)acetylsalicylamide, which uses salicylamide and chloroacetyl chloride as raw materials, and ionic liquid (triethylamine hydrochloride-aluminum trichloride) As a solvent and catalyst, react at 45°C to obtain 5-chloroacetylsalicylic amide, and the obtained 5-chloroacetylsalicylic amide reacts with dibenzylamine to obtain 5-(N,N-dibenzylamino)acetylsalicylic acid Amide, concrete steps are as follows:

[0027] Add salicylamide (10g, 0.073mol) and 50g of ionic liquid (triethylamine hydrochloride-aluminum chloride) into a three-necked flask, and after stirring evenly, add chloroacetyl chloride (20.43g, 0.18mol) dropwise at room temperature, After the dropwise addition, the oil bath controls the reaction temperature at 45°C for 2-3 hours, and monitors the reaction with TCL. After the reaction is completed, extract with ethyl acetate for 3-4 times, and spin dry the extracted ethyl acetate layer to obtain a white s...

Embodiment 2

[0030] A simple and efficient method for preparing 5-(N,N-dibenzylamino)acetylsalicylamide, which uses salicylamide and chloroacetyl chloride as raw materials, 1,2-dichloroethane as solvent and trichloro Aluminum catalyst, react at 45°C to obtain 5-chloroacetylsalicylicamide, and then react the obtained 5-chloroacetylsalicylicamide with dibenzylamine to obtain 5-(N,N-dibenzylamino)acetyl water Salicylic amide, concrete steps are as follows:

[0031] Add salicylamide (10g, 0.073mol) and 50g of 1,2-dichloroethane into a three-necked flask. After stirring evenly, add 35g of aluminum trichloride (the same quality as that contained in 50g of ionic liquid) ), and then add chloroacetyl chloride (20.43g, 0.18mol) dropwise at room temperature. After the dropwise addition, the oil bath controls the reaction temperature to 45°C for 2-3 hours. TCL monitors the reaction. After the reaction is completed, extract with ethyl acetate 3-4 times, the extracted ethyl acetate layer was spin-dried...

Embodiment 3

[0035] A simple and efficient method for preparing 5-(N,N-dibenzylamino)acetylsalicylamide, which uses salicylamide, chloroacetyl chloride as raw materials, nitrobenzene) as solvent and aluminum trichloride as catalyst , react at 45° C. to obtain 5-chloroacetylsalicylic amide, and then react the obtained 5-chloroacetylsalicylic amide with dibenzylamine to obtain 5-(N, N-dibenzylamino) acetylsalicylic amide, Specific steps are as follows:

[0036]Add salicylamide (10g, 0.073mol) and 50g of nitrobenzene into a three-necked flask. After stirring evenly, add 35g of aluminum trichloride (the same quality as that contained in 50g of ionic liquid), and then Chloroacetyl chloride (20.43g, 0.18mol) was added dropwise. After the dropwise addition, the oil bath controlled the reaction temperature to 45°C for 2-3 hours. TCL monitored the reaction. After the reaction was completed, extracted 3-4 times with ethyl acetate. The extracted ethyl acetate layer was spin-dried to obtain 9.34 g of...

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Abstract

The invention relates to a preparation method for 5-(N, N-dibenzylamino)acetylsalicylamide. The method includes: adding salicylamide and chloroacetyl chloride into a container to carry out reaction according to a mole ratio of 1: 2.5-5.5, using an ionic liquid as the solvent, with the mole ratio of the ionic liquid to salicylamide being 5-10:1, carrying out reaction at 35-55DEG C under atmospheric pressure, then at the end of the reaction, taking an organic solvent to perform extraction to obtain 5-chloracetylsalicylamide, adding the prepared 5-chloracetylsalicylamide and dibenzylamine into a mixed solution of water and methanol, with the volume ratio of methanol to water being 2-4:1, carrying out heating reaction at 50-70DEG C for 2-4h, with 5-chloracetylsalicylamide and dibenzylamine being in a mole ratio of 1:1.0-1.2, at the end of the reaction, conducting vacuum distillation to remove the solvent, and performing recrystallization to obtain 5-(N, N-dibenzylamino)acetylsalicylamide. The preparation method provided by the invention has the characteristics of low production cost, short synthesis step, high yield, and small environmental pollution.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a 5-(N,N-dibenzylamino)acetylsalicylic amide, specifically a 5-(N,N-dibenzylamino)acetylsalicylic amide Preparation. Background technique [0002] 5-(N,N-dibenzylamino) acetylsalicylamide is an adrenergic receptor blocker and one of the important intermediates in the drug synthesis of Labetalol (Labetalol, also known as benzylamine). Labetalol is an alpha and beta adrenoceptor blocker. It selectively blocks α receptors, and at the same time blocks β receptors. The ratio of α to β receptor blockade is 1:6.9 during intravenous injection. It has a stronger effect on β receptors and can slow down A-V conduction, while reducing blood pressure, can slow down the heart rate, reduce the cardiac output, and increase the coronary flow. Peripheral vascular resistance continued to decrease, hemodynamics showed benign changes, and there was no significant effect on serum lipids, lipoprotei...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/30C07C231/12
CPCY02P20/54
Inventor 姚志艺宗豪强吴云龙李彩红李争峰李星张晓攀
Owner SHANGHAI INST OF TECH
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