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Preparation method of aminomethylbenzoic acid

A technology of aminotoluic acid and chloromethylbenzoic acid is applied in the preparation of carboxylates, the preparation of organic compounds, the preparation of cyanide reactions, etc., and can solve the problem that the reaction system is difficult to handle, the chlorine chlorination efficiency is low, and the overall yield is low. and other problems, to achieve the effect of low production cost, low production cost and high overall yield

Inactive Publication Date: 2020-12-08
山东诚汇双达药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this process, the chlorination efficiency of chlorine gas is low, and a large amount of dichlorinated products are produced, which makes the reaction system difficult to handle, and the overall yield of the reaction is low
(3) Patent CN201510338012.X uses p-cyanobenzyl chloride as the starting material to prepare aminotoluic acid through ammonolysis and hydrolysis. However, the cost is high because the raw material p-cyanobenzyl chloride is not easy to obtain
In the recovery process of hydrogen bromide in this process, a large amount of solvents, acid and alkali reagents are used, and a large amount of solid salt is produced, which is difficult to handle

Method used

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  • Preparation method of aminomethylbenzoic acid

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Effect test

Embodiment 1

[0039] (1) Synthesis of intermediate p-chloromethylbenzoic acid (II):

[0040] Dissolve p-toluic acid (490g) and azobisisobutyronitrile (8.52g) in dichloroethane (2200g), raise the temperature of the reaction system to 50-60°C, then add dropwise at a temperature of 30-100°C Sulfonyl chloride (1000g), a large amount of gas will be released after the reaction is triggered, and the dropping rate should be controlled to prevent material flushing. After the reaction system is reacted at 50-60°C for 3-4 hours, less than 5% of the raw materials remain. The reaction system was concentrated to dryness under reduced pressure, and the obtained fractions were recovered and used mechanically (the recovery rate was more than 70%), and the obtained solids were directly used in the next step without purification.

[0041] (2) Synthesis of aminomethylbenzoic acid (III)

[0042] Dissolve the solid (612g) obtained in step (1) in a mixed solvent of methanol (1200g) and water (270g), add urotrop...

Embodiment 2

[0044] (1) Synthesis of intermediate p-chloromethylbenzoic acid (II):

[0045] Dissolve p-toluic acid (100 kg) and azobisisobutyronitrile (1.74 kg) in dichloroethane (450 kg), raise the temperature of the reaction system to 50-60°C, and then control the temperature to 30-100°C Add sulfuryl chloride (204 kg) dropwise, a large amount of gas will be released after the reaction is initiated, and the dropping rate should be controlled to prevent material flushing. After the reaction system is reacted at 50-60°C for 4-6 hours, less than 5% of the raw materials remain. The reaction system was concentrated to dryness under reduced pressure, and the obtained fractions were recovered and used mechanically (the recovery rate was more than 75%), and the obtained solids were directly used in the next step without purification.

[0046] (2) Synthesis of aminomethylbenzoic acid (III)

[0047] Dissolve the solid obtained in step (1) in a mixed solvent of methanol (245 kg) and water (55 kg), a...

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of aminomethylbenzoic acid. The method comprises the following steps: carrying outchlorination reaction on p-toluic acid and a chlorination reagent under the condition of a catalyst I to obtain an intermediate p-chloromethylbenzoic acid, and carrying out ammonolysis on the intermediate p-chloromethylbenzoic acid and ammonia water under the condition of a catalyst II to prepare aminomethylbenzoic acid. The purity of the obtained product aminomethylbenzoic acid is greater than 99.9%, the single impurity content is less than 0.1%, and the overall yield of the two-step reaction is greater than 63%. The method is short in synthetic route, free of highly toxic reagents or precious metals, low in production cost, less in environmental pollution, high in overall yield and suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of aminotoluic acid. Background technique [0002] The chemical name of aminotoluic acid is 4-aminomethylbenzoic acid (structure shown in formula III), and it is mainly used in the form of monohydrate for medicinal purposes. Its hydrate is white scaly or crystalline powder, odorless, slightly bitter taste, slightly soluble in water, but soluble in boiling water, almost insoluble in organic solvents such as ethanol, ether, and chloroform. [0003] [0004] Aminomethylbenzoic acid (also known as hemostatic aromatic acid) is a procoagulant drug, which is mainly used clinically for acute and chronic, localized or systemic hemorrhage caused by primary fibrin excessive dissolution, specifically It can be used for abnormal bleeding during operations on the lung, liver, pancreas, prostate, thyroid, adrenal gland, etc., obstetrics and gyneco...

Claims

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Application Information

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IPC IPC(8): C07C227/08C07C229/38C07C51/363C07C63/70
CPCC07C51/363C07C227/08C07C63/70C07C229/38
Inventor 王延斌吕志波王胜秦艳芳黄凤芸谭光明
Owner 山东诚汇双达药业有限公司
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