Preparation method of 2-(methyl sulphonyl)-10H-phenothiazine

A technology of methylsulfonyl and phenothiazine, which is applied in the field of preparation of 2--10H-phenothiazine, can solve problems such as high cost, unfavorable industrialized production, etc., and achieves improved yield, environmental protection, and increased contact area effect

Inactive Publication Date: 2016-08-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Wherein the yield obtained by the first route is 49%, the yield of the latter two routes is less than 49%, and the raw materials of the three synthetic routes are phenothiazine compounds, the cost is relatively high, which is not conducive to industrial production

Method used

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  • Preparation method of 2-(methyl sulphonyl)-10H-phenothiazine
  • Preparation method of 2-(methyl sulphonyl)-10H-phenothiazine
  • Preparation method of 2-(methyl sulphonyl)-10H-phenothiazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis of p-chlorophenylsulfone (2a)

[0049]

[0050] In a 250ml three-neck round bottom flask equipped with a stirrer, dropping funnel, thermometer and tail gas recovery device, add 21.2g of sodium sulfite, 26.5g of sodium bicarbonate, and 100ml of water, raise the temperature to 75°C while stirring, and weigh 31.2 Add 4 g of p-chlorobenzenesulfonyl chloride to the three-necked flask in batches within 3 hours, keep warm and reduce for 1 hour, slowly add (35.9g sodium chloroacetate dissolved in 50ml water) aqueous solution of sodium chloroacetate dropwise through the constant pressure dropping funnel, and the temperature of the mixture is raised to 105 -107°C, reflux reaction for 15h, after the reaction, pour out the reactant, cool, filter with suction, pour the solid into a beaker, add an appropriate amount of CCl 4 Carry out purification, stand overnight and then suction filter, put into vacuum drying box and dry, obtain white needle-like crystal, we...

Embodiment 2

[0053] Example 2: Synthesis of 2-nitro-4-thiamphenicol chlorobenzene (2b)

[0054]

[0055] In a 100ml three-neck round bottom flask equipped with a stirring dropping funnel, a thermometer and a stirrer, add 24ml of concentrated sulfuric acid and 11.3g of p-chlorophenylsulfone, stir to dissolve p-chlorophenylsulfone, and slowly Add 6ml of nitric acid dropwise. After the dropwise addition, keep the temperature at 25°C and keep it warm for 2 hours. Then pour the reaction solution into a beaker, add an appropriate amount of ice water into the beaker while stirring, and a white precipitate will precipitate. Cool to room temperature and wash with suction. After deacidification and vacuum drying, a white powdery solid was obtained, which weighed 13.9 g. The melting range was 124.2-125.1°C as determined by the melting point apparatus. The purity was 99.9% and the yield was 99.7% as determined by the gas phase.

[0056] Each hydrogen atom belongs to: 1 H NMR (500M, CDCl 3 ) : δ:...

Embodiment 3

[0059] Example 3: Synthesis of Compound M1

[0060]

[0061] In a 250ml three-necked round-bottomed flask equipped with a stirrer, dropping funnel, and thermometer, add 23.56g of 3-nitro-p-chlorophenylmethyl sulfone (0.1mol) and 100ml of absolute ethanol in sequence, stir and heat up to 40°C. Dissolve completely, add dropwise a mixed solution of 34.4g 20% ​​sodium ethoxide ethanol solution and 19.21 (0.101mol) g 2-bromothiophenol, and raise the temperature to 80°C at the same time, after about 0.5h dropwise addition, continue to reflux for 24h to stop the reaction, cool to At room temperature, recrystallize with absolute ethanol, collect the product by suction filtration, and dry to obtain 38.47 g of a yellow powder product. The melting range measured by the melting point instrument is 162.4~163.0°C, the purity is 99.9%, and the yield is 99.0%.

[0062] Each hydrogen atom is assigned to δ: 1 HNMR (500M, CDCl 3 ):8.82(s,1H),7.86(d,1H),7.83(d,1H),

[0063] 7.76 (d, 1H), 7...

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Abstract

The invention relates to a preparation method of 2-(methyl sulphonyl)-10H-phenothiazine and belongs to the technical field of medical intermediate preparation. According to the method, parachlorobenzenesulfonyl chloride and sodium salt of 2-bromothiophenol are taken as starting materials, two novel intermediates M1 and M3 not reported are involved, ideal schemes different from related references are explored in all experimental procedures, and particularly the cyclization process for synthesis of the final product 2-(methyl sulphonyl)-10H-phenothiazine completely breaks through various restrictions in literatures. The method has the advantages that the whole process is simple in step, convenient to operate, mild in reaction condition and easy to control, product yield in all the steps is high and the like, thereby being suitable for industrial production and having high value in use and social and economic benefits.

Description

technical field [0001] The invention relates to a preparation method of 2-(methylsulfonyl)-10H-phenothiazine, which belongs to the technical field of preparation of pharmaceutical and chemical intermediates. Which involves two new unreported intermediate products 1-[(2-bromophenyl) mercapto] -4- (methylsulfonyl) -2-nitrobenzene (denoted as compound M1) and N-[2 -(2-Bromophenyl)mercapto]-5-[(methylsulfonyl)-phenyl]formamide (referred to as compound M3). Background technique [0002] Phenothiazine compounds are important chemical products and pharmaceutical intermediates. They have been put into production and operation and have a development history of more than 100 years. As the most primitive synthetic antipsychotic drugs, they have good biological and pharmacological activities. It is effective in the treatment of Parkinson's disease, mental anxiety, depression, malaria, etc., and is commonly used in psychiatric and antihistamine drugs. In addition, phenothiazine compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/20
CPCC07D279/20
Inventor 张华孟海霞
Owner DALIAN UNIV OF TECH
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