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A method for preparing 4-(n-phenothiazine-)-carbonyl-2-butenoic acid

A technology of phenothiazine and crotonic acid, applied in the direction of organic chemistry, can solve the problems of long time, troublesome post-processing, high reaction temperature, etc., and achieve the effect of short reaction time, low equipment requirements and easy availability of raw materials

Active Publication Date: 2016-02-10
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a high reaction temperature and a long time, and the post-treatment is also relatively troublesome.

Method used

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  • A method for preparing 4-(n-phenothiazine-)-carbonyl-2-butenoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In the first step, add 0.0025mol of phenothiazine and 0.0025mol of maleic anhydride to a dry three-necked flask, then add 10mL of acetonitrile, and slowly add 0.2mL of mass concentration to the reaction vessel at a stirring speed of 1500r / min. 36-38% concentrated hydrochloric acid to obtain a reaction solution. The reaction solution was heated from room temperature at a rate of 3 °C / min to 40 °C, and stirred at a rate of 1500 r / min for 2.5 hours to obtain a mixed solution;

[0023] In the second step, the acetonitrile is evaporated from the mixed solution under reduced pressure to obtain a concentrated solution. The volume of acetonitrile in the concentrated solution is 15% of the volume of acetonitrile in the mixed solution. After the concentrated solution is cooled to room temperature, 10 mL of water is added thereto, stirred for 5 minutes, and pumped. Filter, wash the filter cake with water, and dry at room temperature to obtain a white powder that is 4-(N-phenothiazi...

Embodiment 2

[0026] In the first step, add 0.0025mol of phenothiazine and 0.0028mol of maleic anhydride to a dry three-necked flask, then add 10mL of acetonitrile, and slowly add 0.15mL of mass concentration to the reaction vessel at a stirring speed of 2200r / min. 36-38% concentrated hydrochloric acid to obtain a reaction solution, the reaction solution was heated from room temperature at a rate of 4 °C / min to 50 °C, and stirred at a rate of 2200 r / min for 2.5 hours to obtain a mixed solution;

[0027] In the second step, the acetonitrile is evaporated from the mixed solution under reduced pressure to obtain a concentrated solution. The volume of acetonitrile in the concentrated solution is 20% of the volume of acetonitrile in the mixed solution. After the concentrated solution is cooled to room temperature, 10 mL of water is added thereto, stirred for 5 minutes, and pumped. Filter, wash the filter cake with water, and dry at room temperature to obtain a white powder that is 4-(N-phenothiaz...

Embodiment 3

[0029] In the first step, add 0.00250mol of phenothiazine and 0.00275mol of maleic anhydride to a dry three-necked flask, then add 12mL of acetonitrile, and slowly add 0.2mL of mass concentration to the reaction vessel at a stirring speed of 1700r / min. 36-38% concentrated hydrochloric acid to obtain a reaction liquid, the reaction liquid was heated from room temperature at a rate of 3 °C / min to 60 °C, and stirred at a speed of 1700 r / min for 2 hours to obtain a mixed liquid;

[0030] In the second step, the acetonitrile is evaporated from the mixed solution under reduced pressure to obtain a concentrated solution. The volume of acetonitrile in the concentrated solution is 17% of the volume of acetonitrile in the mixed solution. After the concentrated solution is cooled to room temperature, 15 mL of water is added thereto, stirred for 7 minutes, and then pumped. Filter, wash the filter cake with water, and dry at room temperature to obtain a white powder that is 4-(N-phenothiazi...

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Abstract

The invention relates to a method for preparing 4-(N-phenothiazine)-carbonyl-2-butenoic acid. The method comprises the following steps: adding A mol of phenothiazine and B mol of maleic anhydride into a reaction container, and then adding acetonitrile; dripping concentrated hydrochloric acid into the reaction container while stirring to get a reaction solution, increasing the temperature of the reaction solution from room temperature to 40-80 DEG C, and performing reaction for 1-2.5h while stirring to get a mixed solution, wherein A: B=2.5: (2.5-3.0); performing reduced-pressure distillation on the mixed solution to remove acetonitrile to get a concentrated solution, wherein the volume of acetonitrile in the concentrated solution is 15-20% of the volume of acetonitrile in the mixed solution; and cooling the concentrated solution to room temperature, then adding water into the concentrated solution, uniformly stirring, then performing suction filtration, washing a filter cake with water, and drying to get 4-(N-phenothiazine)-carbonyl-2-butenoic acid. According to the method disclosed by the invention, acetonitrile is adopted as a solvent, concentrated hydrochloric acid is taken as a catalyst, and the method has the advantages of simplicity and convenience in operation, short reaction time, mild conditions, simple post-treatment, low price and easiness in obtaining of raw materials and high yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing 4-(N-phenothiazine-)-carbonyl-2-butenoic acid. Background technique [0002] Phenothiazine is a heterocyclic compound containing nitrogen and sulfur, also known as thiazepine or diphenylamine sulfide. Studies have found that phenothiazine and its derivatives have high pharmacological and biological activities. In recent years, Phenothiazine compounds are widely used in industries such as polymerization inhibitors, antioxidants in lubricants, biomedicine, and dyes. In addition, they can also be used in synthetic drugs, fruit tree insecticides, and organic electroluminescent materials. etc. With the continuous exploration of scientific researchers, phenothiazine drugs are suitable for the treatment of acute and chronic schizophrenia, mania and other severe mental illnesses, and can control symptoms such as excitement, aggression, hallucinations and delusion...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D279/30
Inventor 刘玉婷殷艳佼尹大伟付青蒋闪闪粱钢涛
Owner SHAANXI UNIV OF SCI & TECH
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