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4-(N-phenthiazine-)-carbonyl-2-butenoic acid and preparation method thereof

A technology of phenothiazine and crotonic acid, which is applied in the direction of organic chemistry, can solve the problems of no literature reports, etc., and achieve the effect of easy reaction process, high yield and simple post-treatment

Inactive Publication Date: 2014-12-03
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There is no literature report on the compound 4-(N-phenothiazine-)-carbonyl-2-butenoic acid

Method used

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  • 4-(N-phenthiazine-)-carbonyl-2-butenoic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation method of 4-(N-phenothiazine-)-carbonyl-2-butenoic acid comprises the following steps:

[0025] In the first step, add 0.010mol of phenothiazine and 0.013mol of maleic anhydride to the dry reaction flask, and then add 8mL of DMF to obtain a reaction solution; at a stirring speed of 2000r / min, heat the reaction solution to 120°C And keep warm, use TLC to monitor the reaction process, after the raw material point disappears, continue to stir at 120 ° C for 0.5 h to obtain the mixture; wherein the developer of TLC is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:7;

[0026] In the second step, after the mixture is cooled to room temperature, it is poured into a beaker filled with 1.2 mol of water under stirring, suction filtered, washed with water, and dried at room temperature to obtain 2.77 g of white solid which is 4-(N-phenothiazine -)-oxo-2-butenoic acid, the yield was 93.27%. 1 H-NMR (CDCl 3 , 400M, TMS internal stand...

Embodiment 2

[0028] The preparation method of 4-(N-phenothiazine-)-carbonyl-2-butenoic acid comprises the following steps:

[0029] In the first step, add 0.020mol of phenothiazine and 0.021mol of maleic anhydride to the dry reaction flask, and then add 9mL of DMF to obtain a reaction solution; at a stirring speed of 1500r / min, heat the reaction solution to 130°C And keep warm, use TLC to monitor the reaction process, after the raw material point disappears, continue to stir at 130 ° C for 0.5 h to obtain the mixture; wherein the developer of TLC is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:6;

[0030] In the second step, after the mixture is cooled to room temperature, it is poured into a beaker containing 2.0 mol of water under stirring, suction filtered, washed with water, and dried at room temperature to obtain 5.56 g of white solid which is 4-(N-phenothiazine -)-oxo-2-butenoic acid, the yield was 93.60%.

Embodiment 3

[0032] The preparation method of 4-(N-phenothiazine-)-carbonyl-2-butenoic acid comprises the following steps:

[0033] In the first step, add 0.020mol of phenothiazine and 0.022mol of maleic anhydride to the dry reaction flask, and then add 10mL of DMF to obtain a reaction solution; at a stirring speed of 2500r / min, heat the reaction solution to 155°C And keep warm, use TLC to monitor the reaction process, after the raw material point disappears, continue to stir at 155 ° C for 0.5 h to obtain the mixture; wherein the TLC developer is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:8;

[0034] In the second step, after the mixture is cooled to room temperature, it is poured into a beaker containing 1.9 mol of water under stirring, suction filtered, washed with water, and dried at room temperature to obtain 5.55 g of white solid which is 4-(N-phenothiazine -)-oxo-2-butenoic acid, the yield was 93.43%.

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Abstract

The invention discloses 4-(N-phenthiazine-)-carbonyl-2-butenoic acid and a preparation method thereof. A structural formula of 4-(N-phenthiazine-)-carbonyl-2-butenoic acid is as shown in the specification. The preparation method of 4-(N-phenthiazine-)-carbonyl-2-butenoic acid comprises the steps that A mol phenthiazine and B mol maleic anhydride are added to a reaction vessel; then C ml DMF (Dimethyl Formamide) is added; reaction liquid is obtained; the reaction liquid is heated to 100-155 DEG C on a condition of stirring and subjected to heat preservation; TLC (thin layer chromatography) is used for monitoring a reaction process; the reaction liquid is stirred continuously at 100-155 DEG C for 0.5h after raw material points are disappeared; a mixture is obtained, wherein the ratio of A to B to C is equal to 1:(1.0-1.3)-(400-800); after the mixture is cooled to a room temperature, the mixture is poured into water, subjected to suction filtration, washed and dried; and 4-(N-phenthiazine-)-carbonyl-2-butenoic acid is obtained. The method is easy and simple to operate; the reaction process is easy to control; post treatment is simple; and the productivity is high.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to 4-(N-phenothiazine-)-carbonyl-2-butenoic acid and a preparation method thereof. Background technique [0002] Phenothiazine is a heterocyclic compound containing nitrogen and sulfur, also known as thiazepine or diphenylamine sulfide. It is an important class of fine chemical intermediates and plays an important role in many chemical reactions. Phenothiazine derivatives are widely used in pesticides, medicines, veterinary insect repellents, dyes and auxiliary agents for synthetic materials. They are mainly used as raw materials for insect repellants, insecticides and dyes, and can also be used in nonlinear optics, Optoelectronic fields such as electroluminescence and semiconductor devices. With the continuous exploration of scientists, phenothiazine drugs have begun to be suitable for the treatment of acute and chronic schizophrenia, mania, reactive psychosis and othe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D279/30
Inventor 刘玉婷蒋闪闪殷艳佼尹大伟付青吕博
Owner SHAANXI UNIV OF SCI & TECH
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