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Preparation method of 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazine-4-one

A technology of benzoxazine and hydroxyphenyl, which is applied in the field of preparation of 2--4H-[1,3]-benzoxazine-4-one, can solve the problem of difficult manipulation, a large amount of acid-containing waste water, and product loss and other problems, to achieve the effect of simple synthesis process, high practicability and easy operation

Pending Publication Date: 2022-02-25
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The commonly used synthetic method is to use salicylic acid, salicylamide, and thionyl chloride as raw materials to prepare 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazin-4-one, The problems in the route of thionyl chloride are as follows: 1) The route salicylamide is prepared as follows: salicylic acid→salicyloyl→salicylonitrile. In industrial production, the intermediate product must be separated and purified in each step, which leads to the product is lost at every step
2) This route uses a large amount of concentrated sulfuric acid and thionyl chloride, resulting in a large amount of acid-containing wastewater, which cannot meet the increasingly stringent environmental protection requirements
3) Thionyl chloride is difficult to cool, and the feeding is limited, which directly affects the quality and yield of the product, and the control is difficult

Method used

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  • Preparation method of 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazine-4-one
  • Preparation method of 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazine-4-one
  • Preparation method of 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazine-4-one

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Embodiment 1

[0021] 13.8 grams of salicylic acid, salicylic acid, urea, sulfamic acid, and 4-dimethylaminopyridine were fed in a molar ratio of 1:2:1:0.01, 40 mL of toluene was added, heated to 100°C, and reacted for 8 hours. After the reaction, the solvent was concentrated, 17.4 mL of methanol was added for recrystallization, and 18.7 grams of yellow needle-like solids were obtained by filtration and drying, which was characterized by NMR as 2-(2-hydroxyphenyl)-4H-[1,3]-benzene The yield of oxazin-4-one is 78.2%.

Embodiment 2

[0023] 13.8 grams of salicylic acid, salicylic acid, urea, sulfamic acid, and 4-dimethylaminopyridine were fed in a molar ratio of 1:2:1:0.01, 40 mL of o-dichlorobenzene was added, heated to 130°C, and reacted for 6 hours. After the reaction, the solvent was concentrated, 17.4 mL of methanol was added for recrystallization, and 21.8 grams of yellow needle-like solids were obtained by filtration and drying, which was characterized by NMR as 2-(2-hydroxyphenyl)-4H-[1,3]-benzene The yield of oxazin-4-one is 91.2%.

Embodiment 3

[0025] 13.8 grams of salicylic acid, salicylic acid, urea, sulfamic acid, and 4-dimethylaminopyridine are fed according to the molar ratio of 1:2:1:0.01, and 27.6 grams of diphenyl ether are added, heated to 160°C, and reacted for 4 hours . After the reaction, the solvent was concentrated, 17.4 mL of methanol was added for recrystallization, and 21.3 grams of yellow needle-like solids were obtained by filtration and drying, which was characterized by NMR as 2-(2-hydroxyphenyl)-4H-[1,3]-benzene The yield of oxazin-4-one is 83.2%.

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Abstract

The invention discloses a preparation method of a key intermediate (2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazine-4-one) of drug deferasirox that is a novel iron ion chelating agent and is used for treating iron overload caused by multiple blood transfusion. The invention provides the method for preparing an intermediate 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazine-4-one by a one-pot method. The method is simple in synthesis and has huge application potential.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazin-4-one. Background technique [0002] 2-(2-Hydroxyphenyl)-4H-[1,3]-benzoxazin-4-one is an intermediate of the drug deferasirox. Deerasirox is a new type of iron ion chelation agent developed by Novartis in Switzerland to treat iron overload caused by multiple blood transfusions. In 2015, the US FDA approved it for children aged two and over. The first-line drug for patients, in 2010, the preparation was imported in China. The invention provides a preparation method of its intermediate 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazin-4-one. [0003] The commonly used synthetic method is to use salicylic acid, salicylamide, and thionyl chloride as raw materials to prepare 2-(2-hydroxyphenyl)-4H-[1,3]-benzoxazin-4-one, The problems in the route of thionyl chloride are as follows: 1) The route salicylamide ...

Claims

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Application Information

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IPC IPC(8): C07D265/22
CPCC07D265/22Y02P20/55
Inventor 付永丰高爱红徐婷杨旭高修正
Owner QINGDAO UNIV OF SCI & TECH