Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing N-acyl phenothiazine

A technology of acyl phenothiazine and phenothiazine, which is applied in the field of preparing N-acyl phenothiazine, can solve the problems of long reaction process time, troublesome post-processing, environmental pollution, etc., and achieve short reaction time, small environmental pollution, and post-processing Handle simple effects

Inactive Publication Date: 2014-10-22
SHAANXI UNIV OF SCI & TECH
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction process takes a long time, and many organic solvents are used in the reaction process, which causes serious environmental pollution and troublesome post-processing

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing N-acyl phenothiazine
  • Method for preparing N-acyl phenothiazine
  • Method for preparing N-acyl phenothiazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 0.0055mol benzoic acid and 0.0055mol phosphorus oxychloride to a dry mortar, grind for 0.5h at room temperature until the grinding is uniform, then add 0.005mol phenothiazine, continue grinding, monitor the reaction with TLC, until the phenothiazine is completely reacted At this time, the raw material point of phenothiazine disappeared, and the grinding was stopped to obtain the product, wherein the developer used for TLC monitoring was a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:3, and then the product was allowed to stand at room temperature for 1h ; Then wash with suction and filter, dry the filter cake at room temperature for 24 hours and then recrystallize with water to obtain N-acylphenylphenothiazine. The yield was 93.1%. The melting point is 150-154°C.

[0028] IR(KBr,cm -1 ):3089cm -1 ,3056cm -1 (Unsaturated C-H); 1671cm -1 (amide); 1596cm -1 , 1502cm -1 , 1472cm -1 (benzene ring vibration absorption peak); 1256cm ...

Embodiment 2

[0030] Add 0.0055mol m-toluic acid and 0.0055mol phosphorus oxychloride to a dry mortar, grind for 1 hour at room temperature until the grinding is uniform, then add 0.005mol phenothiazine, continue grinding, monitor the reaction with TLC, until the phenothiazine Reaction is complete, and now the raw material point of phenothiazine disappears, and the grinding is stopped to obtain the product, wherein the developing agent used for TLC monitoring is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3, and then the product is statically placed at room temperature. Set aside for 0.5h; then wash with water and filter with suction, dry the filter cake at room temperature for 22h and then recrystallize with water to obtain N-acyl m-methylphenylphenothiazine. The yield was 94.4%. The melting point is 110-112°C.

[0031] IR(KBr,cm -1 ):3098cm -1 ,3054cm -1 (Unsaturated C-H); 2994cm -1 ,2911cm -1 (saturated C-H); 1656cm -1 (amide); 1595cm -1 , 1500cm ...

Embodiment 3

[0033] Add 0.005mol p-chlorobenzoic acid and 0.0055mol phosphorus oxychloride to a dry mortar, grind for 0.8h at room temperature until the grinding is uniform, then add 0.005mol phenothiazine, continue grinding, monitor the reaction with TLC, until the phenothiazine Reaction is complete, and now the raw material point of phenothiazine disappears, and the grinding is stopped to obtain the product, wherein the developing agent used for TLC monitoring is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3, and then the product is statically placed at room temperature. Set aside for 0.8h; then wash with water and filter with suction, dry the filter cake at room temperature for 23h and then recrystallize with water to obtain N-acyl p-chlorophenylphenothiazine. The yield was 92.6%. The melting point is 134-139°C.

[0034] IR(KBr,cm -1 ):3089cm -1 , 3024cm -1 (Unsaturated C-H); 1654cm -1 (amide); 1598cm -1 , 1502cm -1 , 1459cm -1 (benzene ring vibra...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to a method for preparing N-acyl phenothiazine. The method comprises the steps of adding A mol of an aromatic acid and B mol of phosphorus oxychloride in a reaction vessel; grinding uniformly; then adding C mol of phenothiazine; grinding continuously until phenothiazine is reacted completely to obtain a product; standing the product; washing the product with water; carrying out suction filtration; drying a filter cake; and carrying out re-crystallization to obtain N-acyl phenothiazine. A ratio of A to B to C is (1-1.2):(1-1.2):1. A synthetic method of solid phase grinding is adopted to grind reactants directly for reaction. The method is mild in conditions, short in reaction time and obvious in reaction phenomena, is in no need of solvent, and has small pollution to an environment. The method is simple and convenient for operations; reactions can be carried out only by grinding; and requirements for equipment are low. The yield of a target product can reach over 92%. The method is a simple and convenient method for preparing N-acyl phenothiazine.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing N-acyl phenothiazine. Background technique [0002] Phenothiazines are a class of compounds based on phenothiazine rings. They are mainly used for antipsychotic treatment in clinical practice. The commonly used ones are chlorpromazine, fluphenazine and trifluoperazine (TFP). Plasma protein binding, the concentration in the brain can reach 10 times the plasma concentration. Since the 1960s, the role of such drugs in tumor treatment has gradually been paid attention to and researched. A large number of in vitro studies have shown that phenothiazines have inhibitory effects on the growth and proliferation of various normal cells and tumor cells. . Some recent studies have found that phenothiazines (within the plasma concentration range of 2.36ttmol / L corresponding to the commonly used clinical dose H'correction) can significantly reduce the viability of leu...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D279/30C07D417/06
CPCC07D279/30C07D417/06
Inventor 尹大伟刘蓓蓓刘玉婷靖春燕张晓莉杨阿宁王金玉宋思梦
Owner SHAANXI UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com