Synthetic method for oxyphenbutazone drug intermediate-4-hydroxyazobenzene

A technology of hydroxyazobenzene and hydroxybutazone, applied in organic chemistry and other directions, can solve problems such as weak antipyretic and analgesic effects, and achieve the effects of reducing reaction temperature and reaction time, reducing intermediate links and improving reaction yield.

Inactive Publication Date: 2016-05-25
CHENGDU ZHONGHENG HUATIE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the antipyretic and analgesic effect is weak, while the anti-inflammatory effect is strong, and the effect on inflammatory pain is better

Method used

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  • Synthetic method for oxyphenbutazone drug intermediate-4-hydroxyazobenzene

Examples

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Effect test

example 1

[0013] (i) Add 300ml of sulfuric acid solution with a mass fraction of 5% in the reaction vessel equipped with agitator, thermometer and dropping funnel, control the stirring speed at 100rpm, slowly add 1.2mol of aniline, and reduce the solution temperature to 6°C after completely dissolving, Add dropwise 1.1 mol of potassium bisulfite dissolved in 200 ml of water to form a solution. During the dissolution process, the temperature of the solution is controlled at 6° C., and the end point of the reaction is measured with potassium iodide test paper to generate diazonium salt (3);

[0014] (ii) Add 2L of potassium carbonate solution with a mass fraction of 6% and 1.2mol of phenol in another container to form a potassium phenate solution, slowly add the diazotization solution obtained in step (i) at a speed of 100 rpm, Control the temperature of the solution at 16°C, continue to react for 30 minutes after adding, add the adjusting solution to keep the pH of the solution at 9, then...

example 2

[0016] (i) Add 300ml of sulfuric acid solution with a mass fraction of 7% in the reaction vessel equipped with stirrer, thermometer and dropping funnel, control the stirring speed at 150rpm, slowly add 1.2mol of aniline, and reduce the solution temperature to 7°C after completely dissolving, Add dropwise 1.1 mol of potassium bisulfite dissolved in 220 ml of water to form a solution. During the dissolution process, the temperature of the solution is controlled at 7° C., and the end point of the reaction is measured with potassium iodide test paper to generate diazonium salt (3);

[0017] (ii) Add 2.1 L of potassium carbonate solution with a mass fraction of 8% and 1.2 mol of phenol in another container to form a potassium phenate solution, and slowly add the diazotization solution obtained in step (i) at a stirring speed of 130 rpm , control the temperature of the solution at 18°C, continue to react for 35 minutes after adding, add the adjusting solution to keep the pH of the so...

example 3

[0019] (i) Add 300ml of sulfuric acid solution with a mass fraction of 10% in the reaction vessel equipped with stirrer, thermometer and dropping funnel, control the stirring speed at 200rpm, slowly add 1.2mol of aniline, and reduce the solution temperature to 9°C after completely dissolving, Add dropwise 1.1 mol of potassium bisulfite dissolved in 230 ml of water to form a solution. During the dissolution process, the temperature of the solution is controlled at 8° C., and the end point of the reaction is measured with potassium iodide test paper to generate diazonium salt (3);

[0020] (ii) Add 2.3 L of potassium carbonate solution with a mass fraction of 9% and 1.2 mol of phenol in another container to form a potassium phenate solution, slowly add the diazotization solution obtained in step (i) at a stirring speed of 160 rpm, Control the temperature of the solution at 20°C, continue to react for 40 minutes after adding, add the adjusting solution to keep the pH of the soluti...

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Abstract

The invention discloses a synthetic method for an oxyphenbutazone drug intermediate-4-hydroxyazobenzene. The method comprises the following steps: (i) adding 300ml of a sulfuric acid solution with a certain concentration into a reaction container equipped with a stirrer, a temperature meter and a drop funnel, controlling the stirring speed to be 100-200rpm, slowly adding 1.2mol of phenylamine, after phenylamine is completely dissolved, cooling the solution to 6-9 DEG C, dropwise adding 1.1mol of potassium bisulfite, performing dissolution in 200-230ml of water to prepare a solution, testing a reaction termination point by using potassium iodide test paper, and generating diazonium salt (3); and (ii) adding 2-2.3L of a potassium carbonate solution with a certain concentration and 1.2mol of phenol into the other container to prepare a potassium phenate solution, slowly adding a diazotization solution obtained in the step (i) at the stirring speed of 100-160rpm, controlling the temperature of the solution to be 16-20 DEG C, after the addition is finished, continuing to react for 30-40 minutes, adding an adjusting solution for maintaining the pH value of the solution to be 8-9, then adding an oxalic acid solution for reducing the pH value to be 2-3, keeping the reaction for 40-50 minutes, performing suction filtration, adding a washing solution, and performing dewatering with a dewatering agent to obtain 4-hydroxyazobenzene.

Description

technical field [0001] The invention relates to a method for synthesizing 4-hydroxyazobenzene, a drug intermediate of hydroxybutazone. Background technique [0002] Hydroxybutazone is used in the treatment of rheumatoid arthritis, rheumatoid arthritis and gout. Continuous administration or interaction with other drugs is often required. For acute lymphangitis of filariasis. The role is similar to aminopyrine. However, the antipyretic and analgesic effect is weak, while the anti-inflammatory effect is strong, and the effect on inflammatory pain is better. It can promote the excretion of uric acid. 4-Hydroxyazobenzene is used as the drug intermediate of hydroxybutazone, and the advantages and disadvantages of its synthesis method are of great economic significance for improving the quality of drug synthesis products and reducing the content of by-products. Contents of the invention [0003] The object of the present invention is to provide a kind of synthetic method of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08
CPCC07C245/08
Inventor 彭响亮
Owner CHENGDU ZHONGHENG HUATIE TECH CO LTD
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