Synthesis method of 4-Hydroxythiobenzamide

A technology of hydroxythiobenzamide and hydroxybenzamide, which is applied in the field of synthesis of p-hydroxythiobenzamide, can solve the problems of difficult industrialization and low processing costs, achieve low cost, easy operation, and realize industrial production Effect

Inactive Publication Date: 2014-11-05
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The technology reported in the above literature all has the problem of being difficult to industrialize. The method provided by the invention has mild reaction, safe operation, low raw material price and easy access, high product purity and yield, and low processing cost. It is p-hydroxythiobenzamide The acquisition of provides a new method, which can be applied to large-scale industrial production

Method used

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  • Synthesis method of 4-Hydroxythiobenzamide
  • Synthesis method of 4-Hydroxythiobenzamide
  • Synthesis method of 4-Hydroxythiobenzamide

Examples

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Effect test

Embodiment 1

[0030] Put 150mL of 28% concentrated ammonia water and 8.6g (0.060mol) of methyl p-hydroxybenzoate in the reaction kettle. Under the condition of stirring, control the temperature at 100-120°C and keep it warm for the reaction. TLC detection shows that the reaction is complete. Concentrate the final reaction solution in a rotary evaporator to twice the amount of the feed, filter and dry to obtain a white solid that is p-hydroxybenzamide 7.63g (0.055mol), yield rate 97.8%, HPLC purity 99.1%

Embodiment 2

[0032] Put 150mL of 28% concentrated ammonia water and 8.6g (0.060mol) of methyl p-hydroxybenzoate in the reaction kettle. Under the condition of stirring, control the temperature at 100-120°C and keep it warm for reaction. TLC detection shows that the reaction is complete. Concentrate the final reaction solution in a rotary evaporator to 1.5 times the amount of feed, and then separate and dry by suction filtration to obtain a white solid that is p-hydroxybenzamide 7.64g (0.056mol), yield 98.0%, HPLC purity 96.3%.

Embodiment 3

[0034] Put 100mL of 28% concentrated ammonia water and 8.6g (0.060mol) of methyl p-hydroxybenzoate in the reaction kettle. Under the condition of stirring, control the temperature at 100~120°C and keep the reaction. TLC detects that the reaction is complete. Concentrate the final reaction liquid in a rotary evaporator to twice the amount of feed, and then separate and dry by suction filtration to obtain 7.54 g (0.055 mol) of white solid p-hydroxybenzamide, with a yield of 96.7% and a purity of 97.2% by HPLC.

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Abstract

The invention discloses a synthesis method of 4-Hydroxythiobenzamide. The method comprises the following steps: mixing methyl p-hydroxybenzoate with stronger ammonia water, carrying out high-temperature reaction inside a reaction kettle, and then carrying out vacuum concentration on the mixture, so as to obtain p-hydroxybenzene formamide; and refluxing p-hydroxybenzene formamide and phosphorus pentasulfide in a solvent, and obtaining the 4-Hydroxythiobenzamide. The method disclosed by the invention is mild in reaction, safe to operate, low in raw material price, easy to obtain, high in product purity and yield, and low in handling expense, a novel method is provided for obtaining the 4-Hydroxythiobenzamide, and the method disclosed by the invention is applicable to industrial mass production.

Description

technical field [0001] The invention belongs to chemical industry, and in particular relates to a synthetic method of p-hydroxythiobenzamide. Background technique [0002] p-Hydroxythiobenzamide, also known as 4-hydroxythiobenzamide, molecular formula: C 7 h 7 NOS, molecular weight: 153.2, it is an important intermediate of febuxostat, a new anti-gout drug. [0003] There are many reports on the synthesis method of p-hydroxythiobenzamide. Chinese patent document CN201210219548.6 discloses a preparation method of p-hydroxythiobenzamide. Specifically, a certain amount of water, p-cyanophenol, sodium hydrosulfide , secondary amine mixed evenly, at a certain temperature, organic weak acid was added dropwise, after the reaction was finished, filtered, and the filter cake was dried to obtain p-hydroxythiobenzamide, the reaction equation is as follows: [0004] [0005] The disadvantage of this method is that the raw materials used are expensive. [0006] As shown in the pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C327/48
Inventor 郑庚修王秋芬马志佳陈环宇刘建坡乔宇王卫
Owner UNIV OF JINAN
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