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

Preparation method of p-methylsulfonyl benzaldehyde

A technology for p-methylsulfonyl and p-chlorobenzaldehyde is applied in the preparation of thiamphenicol pharmaceutical intermediates and in the field of preparation of pharmaceutical intermediates. The effect of short production cycle, short reaction route and easy operation

Active Publication Date: 2012-09-19
SHANDONG HANXING PHARM TECH CO LTD +1
View PDF4 Cites 20 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process has a long reaction route, low yield, high unit consumption, low utilization rate of equipment, cumbersome operation, and high pressure on environmental protection, which is not conducive to industrial production
[0006] Dong Shunkang et al. reported in "China Pharmaceutical Industry Journal" 1979, 05, pages 1-3 that p-toluenesulfonyl chloride, a by-product of sodium saccharin, was used as a raw material to obtain p-methylsulfonyl chloride by reacting with sodium sulfite, sodium bicarbonate and sodium methyl sulfate. Toluene, then brominated and hydrolyzed to obtain 4-thiamphenicol benzaldehyde, the yield is 53%, the process of this method is long and pollutes a lot

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
  • Preparation method of p-methylsulfonyl benzaldehyde
  • Preparation method of p-methylsulfonyl benzaldehyde
  • Preparation method of p-methylsulfonyl benzaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] According to p-chlorobenzaldehyde: sodium methylmercaptide: the mol ratio of tetrabutylammonium bromide is 1: 1.1: 0.025 and carries out following reaction:

[0033] Under stirring conditions, add 20% by mass concentration of sodium methyl mercaptide aqueous solution, tetrabutylammonium bromide, and 250g p-chlorobenzaldehyde to the reaction kettle, control the temperature at 45-50°C for reaction, and monitor the reaction by TLC until p-chlorobenzaldehyde The reaction of benzaldehyde was complete, and the layers were separated after standing to obtain 290 g of yellow oil in the lower layer, and the yield of crude p-methylthiobenzaldehyde was 107.2%.

[0034] According to p-methylthiobenzaldehyde: hydrogen peroxide: sulfuric acid: the mol ratio of sodium tungstate is 1: 2.5: 0.02: 0.015 and proceeds as follows:

[0035] Under stirring, add 50% concentration of hydrogen peroxide, sodium tungstate and sulfuric acid into the reaction kettle, raise the temperature to 40-50°C,...

Embodiment 2

[0039] According to p-chlorobenzaldehyde: sodium methylmercaptide: tetrabutylammonium chloride mol ratio is 1: 2: 0.2 and carry out following operations:

[0040] Add 250g of p-chlorobenzaldehyde, 30% aqueous solution of sodium methyl mercaptide and tetrabutylammonium chloride into the reaction kettle under stirring, raise the temperature to 55-60°C for reaction, monitor by TLC, until the reaction of p-chlorobenzaldehyde is complete, let stand Separate layers to obtain 296 g of yellow oil in the lower layer, and the yield of crude p-methylthiobenzaldehyde is 109.4%.

[0041] According to p-methylthiobenzaldehyde: hydrogen peroxide: sulfuric acid: manganese sulfate mol ratio is 1: 2.5: 0.02: 0.05 and carries out following operations:

[0042] Add 20% concentration of hydrogen peroxide, manganese sulfate and concentrated sulfuric acid into the reaction kettle, stir and heat up to 40-45°C, add the whole batch of crude p-methylthiobenzaldehyde dropwise, control the reaction temper...

Embodiment 3

[0044] According to p-chlorobenzaldehyde: sodium methylmercaptide: tetrabutylammonium iodide mol ratio is 1: 1.5: 0.1 and carry out following operation:

[0045] Add 250g of p-chlorobenzaldehyde, 15% aqueous solution of sodium methyl mercaptide and tetrabutylammonium chloride into the reaction kettle under stirring, raise the temperature to 50-55°C for reaction, monitor by TLC, until the reaction of p-chlorobenzaldehyde is complete, let stand Separate layers to obtain 288 g of yellow oil in the lower layer, and the yield of crude p-methylthiobenzaldehyde is 106.5%.

[0046] According to p-methylthiobenzaldehyde: hydrogen peroxide: sulfuric acid: manganese sulfate mol ratio is 1: 4: 0.1: 0.1 carries out following operation:

[0047] Add 30% concentration of hydrogen peroxide, manganese sulfate and concentrated sulfuric acid into the reaction kettle, stir and heat up to 40-45°C, add the whole batch of crude p-methylthiobenzaldehyde dropwise, control the reaction temperature at 5...

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

No PUM Login to View More

Abstract

The invention discloses a preparation method of p-methylsulfonyl benzaldehyde, which takes p-chlorobenzaldehyde as starting material, and comprises the steps of: enabling the starting material to have reaction with sodium methyl mercaptide water solution under the action of phase transfer catalyst to obtain p-methylthio benzaldehyde; and oxidizing the p-methylthio benzaldehyde by hydrogen peroxide under the action of sulfuric acid and oxidation catalyst to obtain the p-methylsulfonyl benzaldehyde. The preparation method is easy in obtaining of raw material of the p-methylsulfonyl benzaldehyde, simple and convenient in operation, low in cost, high in yield and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of a thiamphenicol pharmaceutical intermediate, and belongs to the field of organic chemistry. Background technique [0002] p-thymphenylbenzaldehyde, CAS No.5398-77-6, molecular structure: [0003] [0004] It is the main intermediate for the production of a new generation of broad-spectrum antibiotic thiamphenicol and its amino compounds. [0005] The existing process uses toluene as a raw material, and undergoes steps such as chlorosulfonation, reduction, methylation, bromination, and hydrolysis to obtain p-thiamphenicol benzaldehyde. The process has a long reaction route, low yield, high unit consumption, low utilization rate of equipment, cumbersome operation and high environmental protection pressure, which is unfavorable for industrialized production. [0006] Dong Shunkang et al. reported in "China Pharmaceutical Industry J...

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): C07C317/24C07C315/02
Inventor 刘伟军王立新张从金徐小英周敦峰刘良有武强阎素花张康华
Owner SHANDONG HANXING PHARM TECH CO LTD
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