Preparing method for 1-(N-alkylphenothizainyl)-1-methyl(H)-2-substituted Schiff base

A technology of alkylphenothiazine and methyl, which is applied in the field of preparation of 1--1-methyl-2-substituted Schiff base, can solve the problems of low yield, large amount of solvent used, long reaction time, etc. To achieve the effects of shortened reaction time, convenience and easy operation, and short reaction time

Active Publication Date: 2016-01-06
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of Schiff base compounds reported in the existing literature mostly uses ethanol, DMF, etc. as the reaction medium, uses acid as the catalyst, and is prepared by conventional heating methods, so there are shortcomings such as long reaction time, low yield, and large solvent usage.

Method used

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  • Preparing method for 1-(N-alkylphenothizainyl)-1-methyl(H)-2-substituted Schiff base
  • Preparing method for 1-(N-alkylphenothizainyl)-1-methyl(H)-2-substituted Schiff base
  • Preparing method for 1-(N-alkylphenothizainyl)-1-methyl(H)-2-substituted Schiff base

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) Add 0.005mol 3-acetyl-10-methylphenothiazine, 0.006mol thiosemicarbazide and 0.006mol p-toluenesulfonic acid to a dry mortar, and grind for 15min at room temperature. At this time, TLC monitoring shows that 3-acetyl The raw material point of -10-methylphenothiazine disappeared, indicating that the raw material was completely reacted, and then left to stand for 30 minutes to obtain a mixture; wherein the developer of TLC was a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3;

[0030] 2) After the mixture was washed with water and suction filtered, 1-(N-methylphenothiazinyl)-1-methyl-2-thiosemicarbazide Schiff base was obtained. m.p.: 162.6-163.7°C, yield 82%.

[0031] figure 1 For the infrared spectrum of the 1-(N-methylphenothiazinyl)-1-methyl-2-thiosemicarbazide Schiff base that embodiment 1 makes, by figure 1 Known: 3563cm -1 、3514cm -1 and 3441cm -1 is the N-H vibrational absorption peak, and at 2932cm -1 、1303cm -1 at -CH 3 T...

Embodiment 2

[0033] 1) Add 0.005mol 3-acetyl-10-ethylphenothiazine, 0.006mol semicarbazide hydrochloride and 0.006mol p-toluenesulfonic acid to a dry mortar, and grind for 16min at room temperature. At this time, TLC monitoring shows that 3-acetyl - The raw material point of 10-ethylphenothiazine disappeared, indicating that the raw material was completely reacted, and then left to stand for 30 minutes to obtain a mixture; wherein the developer of TLC was a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3;

[0034] 2) After the mixture was washed with water and suction filtered, 1-(N-ethylphenothiazinyl)-1-methyl-2-semicarbazide hydrochloride Schiff base was obtained. m.p.: 135.2-138.5°C, yield 86.5%.

[0035] figure 2 For the infrared spectrum of the 1-(N-ethylphenothiazinyl)-1-methyl-2-hydrochloride semicarbazide Schiff base that embodiment 2 makes, by figure 2 Known: 3392cm -1 、3295cm -1 、3160cm -1 The vibrational absorption peak of N-H is at 2964cm -1...

Embodiment 3

[0037] 1) Add 0.005mol 3-formyl-10-methylphenothiazine, 0.006mol thiosemicarbazide and 0.006mol p-toluenesulfonic acid to a dry mortar, and grind for 15min at room temperature. At this time, TLC monitoring shows that 3-formyl The raw material point of -10-methylphenothiazine disappeared, indicating that the raw material was completely reacted, and then left to stand for 30 minutes to obtain a mixture; wherein the developer of TLC was a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3;

[0038] 2) After the mixture was washed with water and suction filtered, 1-(N-methylphenothiazinyl)-1-H-2-thiosemicarbazide Schiff base was obtained. m.p.: 174.2-176.5°C, yield 85.6%.

[0039] image 3 For the infrared spectrum of the 1-(N-methylphenothiazinyl)-1-H-2-thiosemicarbazide Schiff base that embodiment 3 makes, by image 3 Known: 3377cm -1 、3268cm -1 and 3169cm -1 The vibrational absorption peak of N-H is at 2973cm -1 、1332cm -1 at -CH 3 The absorpt...

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Abstract

The invention relates to a preparing method for a 1-(N-alkylphenothizainyl)-1-methyl(H)-2-substituted Schiff base. The preparing method includes the steps that A mol of 3-formyl(acetyl)-N-alkyl phenothiazine, B mol of substituted ammonia and C mol of p-toluenesulfonic acid are added into a dry reaction container and ground on the room temperature condition, TLC is used for monitoring reactions until the raw materials react completely, and a crude product is obtained after standing, wherein the ratio of A:B:C is 1:(1-1.2): (1-1.2); water scrubbing and suction filtration are carried out on the crude product to obtain the 1-(N-alkylphenothizainyl)-1-methyl(H)-2-substituted Schiff base. The solid-phase reactions are involved in the preparing method and short in reaction time and moderate in reaction condition, the preparing method is low in requirement for equipment, easy to operate, simple in aftertreatment, environmentally friendly, economical and efficient and does not need solvent, and the yield of the target product reaches up to 80% or more.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a preparation method of 1-(N-alkylphenothiazinyl)-1-methyl(H)-2-substituted Schiff base. Background technique [0002] Schiff base compounds refer to a class of compounds containing methyleneamine groups obtained by the affinity addition-dehydration reaction of primary amines and active carbonyl compounds. There are N atoms with strong coordination ability in its structure, and the possibility of exocyclic Heteroatoms such as N and S containing lone pairs of electrons, so the Schiff base compound is an organic ligand with excellent performance. Since the metal ion contains an empty d orbital, it can accept the lone electron pair provided by the heteroatom of the ligand, making the metal Coordinate with heteroatoms to form metal complexes. Functionalized Schiff alkali metal complexes have been widely used in many fields due to their stable structures. Schiff base compounds and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/22
CPCC07D279/22
Inventor 刘玉婷黄涛宋思梦尹大伟孙祎梵高凤呼早霞陈璞
Owner SHAANXI UNIV OF SCI & TECH
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