Method for synthesizing 2-acetyl phenothiazine using phenothiazine as raw material

A technique for the synthesis of acetylphenothiazine, which is applied in organic chemistry and other fields, and can solve problems such as low purity, multiple by-products, and low yield of 2-acetylphenothiazine

Active Publication Date: 2016-03-02
TAICANG YUNTONG BIOCHEM ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because there are more positions available for substitution on the benzene ring, that is, substitutions can occur at the 1, 2, 3, and 4 positions, so there are more by-products, resulting in a lower yield of 2-acetylphenothiazine substituted at the target 2 position , the purity is also lower

Method used

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  • Method for synthesizing 2-acetyl phenothiazine using phenothiazine as raw material
  • Method for synthesizing 2-acetyl phenothiazine using phenothiazine as raw material
  • Method for synthesizing 2-acetyl phenothiazine using phenothiazine as raw material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In the reaction vessel, put phenothiazine, 1.05 mass of formic acid (based on the mass of phenothiazine as 1), silicon dioxide with a quality of 0.01 (total mass of phenothiazine and diethyl malonate 1), after stirring the three evenly, the mixture was placed in a microwave oven and the power was adjusted so that the temperature of the reaction mixed raw materials was 70°C. After being heated by microwave radiation to make it react for 8 minutes, the reaction was terminated. Quenched with ice water, filtered with suction, washed the filter cake layer with water until the washing liquid was neutral, moistened with petroleum ether, washed the filter cake layer, and dried in vacuum to obtain N-formylphenothiazine, which was named compound A.

[0024] Put the above compound A in the reaction vessel, the amount of substance is 1.02 acetyl chloride (the amount of substance of compound A is 1), the amount of substance is 3 aluminum trichloride (the amount of substance of compo...

Embodiment 2

[0027] In the reaction vessel, put phenothiazine, 1.14 mass of formic acid (based on the mass of phenothiazine as 1), and a quality of 0.06 silicon dioxide (total mass of phenothiazine and diethyl malonate 1 meter), after the three are stirred evenly, the mixture is placed in a microwave oven and the power is adjusted so that the temperature of the reaction mixed raw materials is 80°C. After being heated by microwave radiation to make it react for 2 minutes, the reaction was terminated. Quenched with ice water, filtered with suction, washed the filter cake layer with water until the washing liquid was neutral, moistened with petroleum ether, washed the filter cake layer, and dried in vacuum to obtain N-formylphenothiazine, which was named compound A.

[0028] Put the above compound A in the reaction vessel, the amount of substance is 1.08 acetyl chloride (the amount of substance of compound A is 1), the amount of substance is 5 aluminum trichloride (the amount of substance of ...

Embodiment 3

[0031] In the reaction vessel, put phenothiazine, 1.10 mass of formic acid (based on the mass of phenothiazine as 1), a quality of 0.035 silicon dioxide (total mass of phenothiazine and diethyl malonate 1 meter), after the three are stirred evenly, the mixture is placed in a microwave oven and the power is adjusted so that the temperature of the reaction mixed raw materials is 75°C. After being heated by microwave radiation to make it react for 5 minutes, the reaction was terminated. Quenched with ice water, filtered with suction, washed the filter cake layer with water until the washing liquid was neutral, moistened with petroleum ether, washed the filter cake layer, and dried in vacuum to obtain N-formylphenothiazine, which was named compound A.

[0032] Put the above compound A in the reaction vessel, the amount of substance is 1.06 acetyl chloride (the amount of substance of compound A is 1), the amount of substance is 4 aluminum trichloride (the amount of substance of com...

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Abstract

The present invention discloses a method for synthesizing 2-acetyl phenothiazine using phenothiazine as a raw material. The method comprises: by using silicon dioxide as a catalyst, heating phenothiazine with formic acid by microwave radiation for a nucleophilic substitution reaction; conducting an electrophilic substitution reaction on the product obtained in the first step and acetyl chloride under catalysis of aluminium trichloride in a dimethyl sulphone solvent; and conducting a hydrolysis reaction on the product obtained in the second step under catalysis of a strong base. According to the method provided by the invention, phenothiazine is used as the raw material, and through N-formylated nucleophilic substitution, electrophilic substitution on benzene rings and hydrolysis of N-acylamino, 2-acetyl phenothiazine is obtained. According to the method disclosed by the invention, secondary amine is formylated in the method to weaken the positioning effect of N atoms on phenyl rings in ortho-position and para-position of the N atoms, so that the leading role of S atoms on the positioning effect in the ortho-position and the para-position of the S atoms s ensured, and the yield of a target product 2-position acetyl substituted product is significantly improved, thereby ensuring the total yield and purity of 2-acetyl phenothiazine.

Description

technical field [0001] The invention relates to the technical field of 2-acetylphenothiazine, in particular to a method for synthesizing 2-acetylphenothiazine by using phenothiazine as a raw material. Background technique [0002] 2-Acetyphenothiazine, CAS No. 6631-94-3, its structure is shown in Formula 1: [0003] As a derivative of phenothiazine, 2-acetylphenothiazine has good pharmacological activity and is widely used in psychiatric and antihistamine drugs. It has certain effects on depression, mental anxiety, malaria, Parkinson's disease, etc. treatment effect. At present, due to the large two-conjugated system in the molecule and the sufficient electron-donating properties of heteroatoms such as N and S, the research on nonlinear optics, photoreduction, electron transfer, energy exchange molecular labeling and nano-modification is very popular. Researches on the synthesis and performance improvement of its copolymer materials are emerging in an endless stream. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/20
CPCC07D279/20
Inventor 张卫东
Owner TAICANG YUNTONG BIOCHEM ENG
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