Method for preparing 2-amino-5-(N-phenothiazinyl)methyl-1,3,4-thiadiazole

A technology based on phenothiazine and methylene phenothiazine, which is applied in the direction of organic chemistry, can solve the problems of inconvenient operation, complicated experimental process, and long reaction time, and achieves small secondary pollution, simple experimental steps, and short reaction time. short effect

Inactive Publication Date: 2013-07-31
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] Synthesis of newer substituted thiadiazolyl and pyrazolyl phenothiazines as potent anti-inflammatory agents published in Oriental Journal of Chemistry, 2010, 26 (2), pp.497-508 by Kumar, Deepak et al., reported the use of phenothiazine, chlorine Ethyl acetate and thiosemicarbazide were used as raw materials to synthesize 2-amino-5-(N-phenothiazinyl)methylene-1,3,4-thiadiazole, but the experimental process was complicated and the reaction Long time, not easy to operate

Method used

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  • Method for preparing 2-amino-5-(N-phenothiazinyl)methyl-1,3,4-thiadiazole

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Embodiment 1

[0025] 1) Add 0.001 mol of N-carboxymethylene phenothiazine (10H-Phenothiazine-10-acetic acid, manufacturer: Shanghai Chemicals Technology Co., Ltd), 0.001 mol of thiosemicarbazide and 10 mL of mass to a dry three-necked flask Concentrated hydrochloric acid with a concentration of 36-38%, turn on the heating and stirring device, and reflux for 4 hours. At this time, TLC detects that the raw material point of N-carboxymethylene phenothiazine disappears, stop the reaction, and obtain a reaction mixture; wherein, TLC The developer is a mixture of ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate and petroleum ether is 1:3;

[0026] 2) After the reaction mixture is cooled to room temperature, adjust the pH value of the reaction mixture to 8 with a 40% aqueous sodium hydroxide solution, then cool the reaction mixture with ice water until solid particles are precipitated, and suction filter to obtain the filter cake Wash with ice water and dry to obtain the cr...

Embodiment 2

[0029] 1) Add 0.001 mol of N-carboxymethylene phenothiazine (10H-Phenothiazine-10-acetic acid, manufacturer: Shanghai Chemicals Technology Co., Ltd), 0.0012 mol of thiosemicarbazide and 11 mL of Concentrated hydrochloric acid with a mass concentration of 36-38%, turn on the heating and stirring device, and reflux for 4 hours. At this time, TLC detects that the raw material point of N-carboxymethylene phenothiazine disappears, stop the reaction, and obtain a reaction mixture; wherein, TLC The developer is a mixture of ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate and petroleum ether is 1:3;

[0030] 2) After the reaction mixture is cooled to room temperature, adjust the pH value of the reaction mixture to 8 with a 40% aqueous sodium hydroxide solution, then cool the reaction mixture with ice water until solid particles are precipitated, and suction filter to obtain the filter cake Wash with ice water and dry to obtain the crude product, which is recry...

Embodiment 3

[0032] 1) Add 0.001 mol of N-carboxymethylene phenothiazine (10H-Phenothiazine-10-acetic acid, manufacturer: Shanghai Chemicals Technology Co., Ltd), 0.0012 mol of thiosemicarbazide and 12 mL of Concentrated hydrochloric acid with a mass concentration of 36-38%, turn on the heating and stirring device, and reflux for 5 hours. At this time, TLC detects that the raw material point of N-carboxymethylene phenothiazine disappears, stop the reaction, and obtain a reaction mixture; wherein, TLC The developer is a mixture of ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate and petroleum ether is 1:3;

[0033] 2) After the reaction mixture is cooled to room temperature, adjust the pH value of the reaction mixture to 8 with a 40% aqueous sodium hydroxide solution, then cool the reaction mixture with ice water until solid particles are precipitated, and suction filter to obtain the filter cake Wash with ice water and dry to obtain the crude product, which is recry...

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Abstract

The invention provides a method for preparing 2-amino-5-(N-phenothiazinyl)methylene-1,3,4-thiadiazole. The2-amino-5-(N-phenothiazinyl)methylene-1,3,4-thiadiazole is obtained by the steps of adding N-carboxyl-methylene-phenothiazine, thiosemicarbazide and concentrated hydrochloric acid into a reactor, then refluxing to obtain a reaction mixture, cooling the reaction mixture to a room temperature, regulating a pH value of the reaction mixture to 8-9 by using a sodium hydroxide aqueous solution, then cooling the reaction mixture until solid particles are precipitated, suction pumping the solid particles to obtain a filter cake, washing the filter cake by ice water and carrying out recrystallization. The method is simple in experimental step and post-treatment, high in yield and small in secondary pollution, is an economic and environment-friendly industrial preparation method, and fits to need of industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing 2-amino-5-(N-phenothiazinyl)methylene-1,3,4-thiadiazole. Background technique [0002] 1,3,4-Thiadiazole derivatives are a class of compounds with a wide range of uses. They have been deeply studied and widely used in the fields of agriculture, industry, and medicine, especially in the research of pharmaceutical synthesis. A breakthrough has been made. 1,3,4-Thiadiazole is an important pharmaceutical intermediate with strong biological activity and pharmacological activity. 1,3,4-Thiadiazole derivatives can be used to prepare antibacterial, anti-anxiety, anti-depression and anti-cancer aspects of drugs. Therefore, 1,3,4-thiadiazole derivatives are the hot spot and focus of research by chemical researchers in recent years. [0003] Synthesis of newer substituted thiadiazolyl and pyrazolyl phenothiazines as potent anti-inflammatory agents publ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06
Inventor 刘玉婷王捷张韩利刘蓓蓓尹大伟吕博
Owner SHAANXI UNIV OF SCI & TECH
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