Preparation method of p-guanidinobenzoic acid hydrochloride

A technology of guanidinobenzoic acid hydrochloride and p-aminobenzoic acid, which is applied in the field of preparation of p-guanidinobenzoic acid hydrochloride, can solve the problems of cumbersome handling, high risk and high risk of using raw materials, and achieve The effect of high raw material safety, strong experimental operability, and short route

Pending Publication Date: 2022-04-12
安徽昊帆生物有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 1. The method of isocyanate and methyl iodide, however, the post-processing of this route is cumbersome and the use of raw materials is dangerous;
[0005] 2. The cyanamide method, but this method is difficult to deal with the three wastes and is not environmentally friendly;
[0006] 3. The method of thiourea and peracetic acid, which has a greater risk due to the use of strong oxidants
[0007] The above three routes all have relatively large limitations in industrial production, and it is urgent to provide a preparation method with short synthetic routes, high safety of raw materials, strong experimental operability, and suitable for industrial production.

Method used

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  • Preparation method of p-guanidinobenzoic acid hydrochloride

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preparation example Construction

[0023] Preparation method of hydrochloride saline hydrochloride, according to an embodiment of the present invention, including:

[0024] The anti-aminobenzoic acid was refluxed to a pyrazole hydrochloride to form the hydrochloride salt of guanidylbenzoic acid.

[0025] That is, the preparation method of the hydrochloride salt of the hydrochloride of the present invention is selected to form a refluxed reaction in the preparation of amino benzoic acid and pyrazole hydrochloride. Hydrochloride.

[0026] The specific reaction process is as follows:

[0027]

[0028] Further, the molar ratio of amino benzoic acid to the pyrazole hydrochloride, for example, 1: (0.8-1.5). Among them, excessive pyrazole hydrochloride is preferably used to promote the reaction, improve the yield. Preferably, the molar ratio of amino benzoic acid to pyrazole hydrochloride has 1: 1.2.

[0029] Among them, the solvent used in the reflux reaction can be, for example, any of acetonitrile, toluene, dichlorom...

Embodiment 1

[0035] EtOAc The hour reaction is over.

[0036] The reaction solution was concentrated to evaporated to evaporated to 90 mL of water, stirred with solid, stir filtered, filter cake was washed over, collect filter cake, dried 70 ° C to give 42.27 g of thrombipanoic acid hydrochloride, 89.5%.

[0037] The reactant was used to confirm the product structure, the data is as follows:

[0038] 1H NMR (Model: Avance III HD 400M, CDCL3, 400MHz): δ = 12.98 (S, 1H), 10.51 (S, 1H), 7.98-7.96 (D, 2H), 7.82 (S, 4H), 7.34-7.32 (D, 2H), the test results are consistent with the structure.

Embodiment 2

[0040] 1 l of reaction bottles were added to aminobenzoic acid (182 g, 1.327 mol, 1.0 eq), pyrazole hydrochloride (233.43 g, 1.593 mol, 1.2eq) to add acetonitrile (550 mL, 3P), heated to 82 ° C back 3 The hour reaction is over.

[0041] The reaction liquid was concentrated to evaporase, cocked 550 ml of water, stirred and stirred with solid, washed with water, and the filter cake was washed once, and dried 70 ° C, to give 261.26 g of guanidylpanoic acid hydrochloride, yield 91.3%.

[0042] The reactant was used to confirm the product structure, the data is as follows:

[0043] 1H NMR (Model: Avance III HD 400M, CDCL3, 400MHz): δ = 12.98 (S, 1H), 10.50 (S, 1H), 7.99-7.96 (D, 2H), 7.82 (S, 4H), 7.34-7.32 (D, 2H), the test results are consistent with the structure.

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Abstract

The invention provides a preparation method of p-guanidinobenzoic acid hydrochloride, which comprises the following step: carrying out reflux reaction on p-aminobenzoic acid and pyrazol formamidine hydrochloride to generate the p-guanidinobenzoic acid hydrochloride. The preparation method provided by the embodiment of the invention has the advantages of short route, high safety of raw materials, strong experimental operability and suitability for industrial production.

Description

Technical field [0001] The present invention relates to the field of chemical synthesis, and more particularly to the preparation method of hydrochloride saline hydrochloride. Background technique [0002] It is an important drug intermediate for hydrochloride hydrochloride for synthesizing non-pancreatitis inhibitors, such as anti-pancreatitis drug card Mors, naphthamir him and other drugs, this kind of drug main treatment Acute necrotizing pancreatitis. [0003] At present, the preparation method of hydrochloride saline hydrochloride is: [0004] First, isocyanate, iodomethane method, however, the route is cumbersome, and the use of raw materials is large; [0005] Second, a single monanine method, however, the method three is difficult to handle, and it is not friendly to environmental protection; [0006] Third, thiourea, peroxyethic acid method, this method is a large risk due to the use of strong oxidant. [0007] The above three routes have large limitations in industrial ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C277/08C07C279/18
Inventor 王桂春刘炼骆浩吕敏杰
Owner 安徽昊帆生物有限公司
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