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Synthetic method for aminomethylbenzoic acid

A technique for the synthesis of aminotoluic acid, which is applied in chemical instruments and methods, the preparation of organic compounds, organic chemistry, etc., can solve problems such as environmental pollution and severe toxicity, and achieve simple and easy-to-obtain raw materials, accelerated reaction rates, and high yields. high effect

Active Publication Date: 2018-10-09
HUNAN UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patent application number CN201510338012.X uses p-cyanobenzyl chloride as raw material, and -CN will be brought into the product during the reaction process, and -CN is highly toxic, and is not suitable as a raw material for the synthesis of pharmaceutical intermediates; and organic The solvent benzene has high toxicity and is easy to cause environmental pollution

Method used

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  • Synthetic method for aminomethylbenzoic acid
  • Synthetic method for aminomethylbenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1) Add methyl 4-chloromethylbenzoate and triethylamine to the reaction vessel, and then add 2mol / L of 2-amino-5-methyl-1,3,4-thiadiol dropwise under stirring Ethanol-water solution of oxadiazole (mass ratio of ethanol and water: 10:1), react at 100°C for 0.5h, after the reaction is complete, evaporate the solution until a large amount of solids are precipitated, cool, filter, and dry to obtain white solid 4-aminomethyl methyl benzoate; wherein, the molar ratio between methyl 4-chloromethylbenzoate, triethylamine and 2-amino-5-methyl-1,3,4-thiadiazole is 1:1.2: 1;

[0039] 2) Add methyl 4-aminomethylbenzoate to concentrated sulfuric acid solution, the molar ratio of sulfuric acid and 4-aminomethylalkylbenzoate is 1:1, stir and react at 50°C for 1.5h, and react After finishing, be cooled to room temperature, add water (the amount of water substance is 20 times of the amount of 4-aminomethylbenzoic acid methyl ester substance), then add sodium hydroxide solution drop by d...

Embodiment 2

[0041] 1) Add ethyl 4-chloromethylbenzoate and triethylamine to the reaction vessel, then add 2mol / L of 2-amino-5-methyl-1,3,4-thiadiol dropwise under stirring Ethanol-water solution of oxadiazole (mass ratio of ethanol and water: 10:1), react at 80°C for 1.5h, after the reaction is complete, evaporate the solution until a large amount of solids are precipitated, cool, filter, and dry to obtain white solid 4-aminomethyl ethyl benzoate; wherein, the molar ratio between ethyl 4-chloromethylbenzoate, triethylamine and 2-amino-5-methyl-1,3,4-thiadiazole is 1:1.5: 1;

[0042]2) Add ethyl 4-aminomethylbenzoate to the concentrated sulfuric acid solution, the molar ratio of sulfuric acid to 4-aminomethylalkylbenzoate is 2:1, stir and react at 80°C for 1h, and the reaction ends Afterwards, be cooled to room temperature, add water (the amount of water substance is 20 times of the amount of 4-aminomethylbenzoic acid methyl ester substance), then add ammoniacal liquor drop by drop under ...

Embodiment 3

[0044] 1) Add ethyl 4-bromomethylbenzoate and triethylamine to the reaction vessel, then add 2mol / L of 2-amino-5-methyl-1,3,4-thiadiol dropwise under stirring Ethanol-water solution of oxadiazole (mass ratio of ethanol and water: 10:1), react at 70°C for 3 hours, after the reaction is complete, evaporate the solution until a large amount of solids are precipitated, cool, filter, and dry to obtain 4-aminomethyl as a white solid Ethyl benzoate; wherein the molar ratio between ethyl 4-bromomethylbenzoate, triethylamine and 2-amino-5-methyl-1,3,4-thiadiazole is 1:2:1 ;

[0045] 2) Add ethyl 4-aminomethylbenzoate to concentrated sulfuric acid solution, the molar ratio of sulfuric acid and 4-aminomethylalkylbenzoate is 3:1, stir and react at 90°C for 0.5h, and react After finishing, be cooled to room temperature, add water (the amount of water substance is 20 times of the amount of 4-aminomethylbenzoic acid methyl ester substance), then add ammoniacal liquor drop by drop under stir...

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Abstract

The invention discloses a synthetic method for aminomethylbenzoic acid. The synthetic method specifically comprises the following steps: adding 4-halomethyl alkyl benzoate and triethylamine, dropwiseadding ethanol-water solution in which 2-amino-5-methyl-1,3,4-thiadiazole is dissolved while stirring, after a reaction is completed, evaporating solution until a lot of solids are separated out, cooling, filtering, and drying to obtain 4-aminomethyl alkyl benzoate; adding the 4-aminomethyl alkyl benzoate to acid solution, reacting by stirring, cooling, adding water, and dropwise adding alkali until the solution is alkaline, and a lot of the solids are separated out, filtering, washing, and drying to obtain the aminomethylbenzoic acid. The synthetic method is moderate in reaction conditions, less in side reactions, high in yield, low in cost, short in reaction and post-processing time, low in energy consumption, high in production efficiency, small in environmental pollution, and simple in'three wastes' treatment, and suitable for the industrial production. -CN with strong toxicity and an organic solvent with strong pollution are not used, and reaction raw materials are cheap in priceand easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of aminomethylbenzoic acid. Background technique [0002] The chemical name of aminomethylbenzoic acid is 4-aminomethylbenzoic acid, which is white scaly crystal or crystalline powder. Slightly soluble in cold water, soluble in hot water, almost insoluble in ethanol and chloroform. [0003] [0004] Aminomethylbenzoic acid is a hemostatic drug for various bleeding caused by hyperfibrinolysis. At the same time, it is also widely used in whitening skin care products because it can effectively prevent and improve the pigmentation of skin color. Aminomethylbenzoic acid is widely used in surgery and bleeding caused by hyperfibrinolysis in internal diseases. It is suitable for abnormal bleeding in operations on the lung, liver, pancreas, prostate, thyroid, adrenal gland, obstetrics and gynecology, postpartum hemorrhage, tuberculosis hemopty...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/18C07C229/38
CPCC07C227/08C07C227/18C07C229/38
Inventor 黄小兵申有名张向阳刘喜汪仕杰唐轶群罗玲玲
Owner HUNAN UNIV OF ARTS & SCI
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