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Synthesis method of benzamidine hydrochloride

A technology of benzamidine hydrochloride and synthesis method, which is applied in the field of synthesis of benzamidine hydrochloride, can solve problems such as long reaction time, environmental pollution, and slow ammonolysis reaction, and achieve easy industrial production, simple and safe operation , the effect of short synthetic route

Inactive Publication Date: 2017-11-17
CHANGZHOU TIANHUA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process has a high yield, but in the whole process, hydrogen chloride gas is used to catalyze and ammonia gas is used for ammonolysis reaction, which is inconvenient to operate and easily leads to gas leakage and environmental pollution.
[0006] (2) Take benzonitrile as raw material, methanol as solvent, sodium methylate as catalyst to obtain methyl ester hydrochloride, then add ammonium chloride solid ammonolysis to obtain benzamidine hydrochloride, this process does not use hydrogen chloride, ammonia It is more environmentally friendly, but the ammonolysis reaction is slow and the reaction time is long, and it needs to use sodium methoxide and anhydrous ammonium chloride as raw materials. This raw material needs an anhydrous environment to achieve a relatively ideal yield and reaction Conditions are difficult to control

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0023] Synthesis of Benzamidine Oxime

[0024] Hydroxylamine hydrochloride (91.7g, 1.32mol, 1.1eq), water (180mL), benzyltriethylammonium chloride (13.7g, 0.06mol, 0.05eq) were added to a 1L four-necked flask, stirred at room temperature to dissolve, Then add benzonitrile (124g, 1.2mol, 1.0eq), and at a temperature of 10°C, add 30% NaOH (336g) therein for about 1h, then heat up to 40°C, keep the temperature for 6h, and monitor by TLC Raw material disappears (V PE / EA =5:1), after the reaction is completed, cool the reaction solution to 5°C, add 2N dilute hydrochloric acid to adjust the pH=6 to 7, solid precipitates, filter, and dry under vacuum at 50°C to obtain 131g of benzamidine oxime with a yield of 80.2%. m.p: 77-80°C, purity 98.3%.

[0025] Synthesis of Benzamidine Hydrochloride

[0026] Add benzamidine oxime (109g, 0.8mol, 1.0eq), isopropanol (300mL), and glacial acetic acid (120mL) into a 1L four-neck flask, heat up to 50°C, and then add reduced Zn powder (104g, ...

Embodiment 2

[0028] Synthesis of Benzamidine Oxime

[0029] Hydroxylamine hydrochloride (208.5g, 3.0mol, 1.2eq), water (400mL), PEG-2000 (13.7g, 0.06mol, 0.05eq), potassium carbonate (517.5g, 3.75mol, 1.5eq) were added to a 2L In the flask, stir at room temperature for 30min, then slowly add benzonitrile (257.8g, 2.5mol, 1.0eq) to it, after the addition is complete, heat up to 50°C and keep it warm for 4h, TLC monitors that the raw material disappears (V PE / EA =5:1), after the completion of the reaction, cool the reaction solution to 5°C, add 2N dilute hydrochloric acid to adjust the pH=6-7, solid precipitates, filter, and dry under vacuum at 50°C to obtain 293.4g of benzamidine oxime, with a yield of 86.2%. Determination of m.p: 78 ~ 80 ℃, purity 98.7%.

[0030] Synthesis of Benzamidine Hydrochloride

[0031] Benzamidine oxime (272g, 2.0mol, 1.0eq), methyl alcohol (500mL), Raney Ni (15g) were joined in the autoclave of 1L, charged with a small amount of liquid ammonia, N 2 Replaced ...

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PUM

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Abstract

The invention discloses a synthesis method of benzamidine hydrochloride, and belongs to the field of chemical synthesis. Benzonitrile and hydroxylamine hydrochloride carry out addition reactions under the effect of an acid-binding agent and a phase transfer agent to obtain benzamidoxime; obtained benzamidoxime carries out reduction reactions at first and then is acidified to obtain a coarse product of benzamidine hydrochloride; then the coarse product is heated and dissolved in a solvent, active carbon is added into the solution to carry out color removal, then the solution is filtered, and the filtrate is dried to obtain pure benzamidine hydrochloride. The preparation method has the advantages of simpleness, green, environmental friendliness, and suitability for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of benzamidine hydrochloride. Background technique [0002] Amidines are nitrogen-substituted carboxylic acid analogs, and some amidine compounds are fragments of physiologically active substances; at the same time, amidine compounds are also important pesticides and pharmaceutical intermediates, widely used in insect repellents and broad-spectrum acaricides, antibiotics , diuretic, anti-inflammatory drug synthesis. [0003] Benzamidine hydrochloride (benzamidine hydrochloride), also known as benzamidine hydrochloride, can be used as a proteolysis inhibitor, and can also be used as an important raw material for the synthesis of photoaccelerator 1,2,4-thiazole compounds. Therefore, it has a wide range of uses. [0004] The synthetic method of benzamidine hydrochloride mainly contains following two kinds of methods at present: concrete is following...

Claims

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Application Information

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IPC IPC(8): C07C257/18
CPCC07C257/18
Inventor 李光文李剑平倪国成
Owner CHANGZHOU TIANHUA PHARMA
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