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Method for preparing 3-acetyl-10-alkyl phenothiazine

A technology of alkyl phenothiazine and acetyl, which is applied in the field of preparing 3-acetyl-10-alkyl phenothiazine, can solve the problems of high raw material cost, long reaction time, cumbersome process, etc., and achieve short reaction time, The effect of simple reaction process and simple post-processing operation

Inactive Publication Date: 2013-07-24
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The cost of raw materials used in this method is high, the process is loaded down with trivial details, and the reaction time is long

Method used

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  • Method for preparing 3-acetyl-10-alkyl phenothiazine

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Experimental program
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Effect test

Embodiment 1

[0022] In the first step, add 1 mol of 10-methylphenothiazine, 7.1 mol of acetic anhydride and 1.0 mol of phosphoric acid into a dry three-necked flask, and react at 20°C for 2 hours to obtain a reaction solution;

[0023] The second step is to cool the reaction liquid to room temperature, pour it into 8mL water, filter after the solid is precipitated, wash the filter cake with water, and dry it with a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:5. Recrystallize the filter cake to obtain 3-acetyl-10-methylphenothiazine with a yield of 85.5%.

[0024] IR (υ max , KBr, cm -1 ): 3050, 2976, 1725, 1324, 765. 1 HNMR (δppm, CDCl 3 ):2.35(s,3H,-COCH 3 ),3.41(s,3H,-CH 3 ), 6.83-7.75 (m, 7H, Ar-H).

Embodiment 2

[0026] In the first step, add 1 mol of 10-methylphenothiazine, 7.5 mol of acetic anhydride and 2.5 mol of phosphoric acid into a dry three-necked flask, and react at 50°C for 1 hour to obtain a reaction solution;

[0027] The second step is to cool the reaction liquid to room temperature, pour it into 10mL water, filter after the solid is precipitated, wash the filter cake with water, and dry it with a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:5. Recrystallize the filter cake to obtain 3-acetyl-10-methylphenothiazine with a yield of 90.0%.

Embodiment 3

[0029] In the first step, add 1 mol of 10-methylphenothiazine, 8.9 mol of acetic anhydride and 2.5 mol of phosphoric acid into a dry three-necked flask, and react at 60°C for 1.5 hours to obtain a reaction solution;

[0030] The second step is to cool the reaction solution to room temperature, pour it into 12mL water, filter after the solid is precipitated, wash the filter cake with water, and dry it with a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:5. Recrystallize the filter cake to obtain 3-acetyl-10-methylphenothiazine with a yield of 87.6%.

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Abstract

The invention provides a method for preparing 3-acetyl-10-alkyl phenothiazine. The method comprises the following steps of: 1, adding A mol of 10-alkyl phenothiazine and B mol of acetic anhydride to a reaction vessel; then adding phosphoric acid; reacting for 0.5 to 2 hours at 20 to 60 DEG C to obtain a reaction liquid, wherein the ratio of A to B is 1: (7-10); 2, cooling the reaction liquid to room temperature; adding the reaction liquid to water; filtering after a solid is separated; washing and drying a filter cake; and then recrystallizing, thus obtaining the 3-acetyl-10-alkyl phenothiazine. The method does not need a solvent for reaction, the reaction process is simple, the reaction time is short, the reaction condition is mild, the requirement on equipment is low, the post-processing operation is simple, the yield of the 3-acetyl-10-alkyl phenothiazine is relatively high, and the method is an economic, convenient and efficient method for preparing the 3-acetyl-10-alkyl phenothiazine.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing 3-acetyl-10-alkylphenothiazines. Background technique [0002] Phenothiazine has been widely concerned by researchers since its synthesis, because of its high pharmacological activity, anti-oxidation, photoluminescence and other properties. Among them, alkylated phenothiazines are not only widely used in the treatment of diseases such as Parkinson's disease and malaria, but also in the lubricating oil of aero-engines, occupying an important position in chemical synthesis. Therefore, in recent years, N-alkylated phenothiazines and their derivatives have become a major research hotspot in medicinal chemistry, attracting the attention of chemists at home and abroad. [0003] Lai, Rebecca Y et al. used acetyl chloride as an acylating reagent, aluminum trichloride as a catalyst, and carbon disulfide as a solvent in Journal of the American Chemical Society, 200...

Claims

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Application Information

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IPC IPC(8): C07D279/22
Inventor 刘玉婷刘蓓蓓蒋闪闪尹大伟梁钢涛付青
Owner SHAANXI UNIV OF SCI & TECH
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