Unlock instant, AI-driven research and patent intelligence for your innovation.

A method for preparing α-acyloxysulfide derivatives

A technology for acyloxy sulfide and derivatives, which is applied in the field of preparing α-acyloxy sulfide derivatives, can solve the problems of low yield and high toxicity of sulfoxide raw materials, and achieves the effects of reducing cost and solving low yield

Active Publication Date: 2022-03-08
CHANGZHOU UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a method for preparing α-acyloxysulfide derivatives, which follows the purpose of green chemistry, and solves the problem of low yield and high toxicity of sulfoxide raw materials in the traditional preparation of α-acyloxysulfide derivatives and other problems, while the catalyst reaction process used in the present invention is simple and the product yield is high, thereby greatly reducing the cost of preparing α-acyloxysulfide derivatives, which has industrial value

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
  • A method for preparing α-acyloxysulfide derivatives
  • A method for preparing α-acyloxysulfide derivatives
  • A method for preparing α-acyloxysulfide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: α-acyloxysulfide derivatives—[(2-n-butylcarbamoylphenyl)thio]methyl acetate and its preparation method

[0040] [(2-substituted carbamoylphenyl) thio] methyl carboxylate, its structural formula is as follows:

[0041]

[0042] Its preparation method is as follows:

[0043] Add acetonitrile (10mL), N-n-butyl-2-methylthiobenzamide (1.0mmol, 0.223g), acetic acid (1.0mmol, 0.060g), sodium acetate (3.0mmol, 0.246 g) and Selectfluor (1.0 mmol, 0.355 g), the reaction temperature was controlled at 120° C., and the reaction was vigorously stirred for 24 hours. After the reaction was completed, the reaction liquid was concentrated and separated by column chromatography in sequence to obtain methyl [(2-n-butylcarbamoylphenyl)thio]acetate with a yield of 0.244 g and a yield of 87%.

[0044] The reaction formula is as follows:

[0045]

Embodiment 2

[0046] Embodiment 2: The preparation method of α-acyloxysulfide derivative—[(2-substituted carbamoylphenyl)thio]carboxylate methyl ester is as follows:

[0047] Synthesis of [(2-substituted carbamoylphenyl) thio] carboxylate methyl ester: Add acetonitrile (10 mL), N-substituted-2-methylthiobenzamide (1.0 mmol , 0.223g), carboxylic acid B (1.0mmol), sodium salt of carboxylic acid B (3.0mmol) and Selectfluor (1.0mmol, 0.355g), the reaction temperature was controlled at 120°C, and the reaction was vigorously stirred for 24 hours. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography in sequence to obtain methyl [(2-substituted carbamoylphenyl)thio]carboxylate.

Embodiment 3

[0048] Example 3: α-acyloxysulfide derivatives—[(2-phenylcarbamoylphenyl)thio]acetic acid methyl ester and its preparation method

[0049] Adopt the preparation method of embodiment 1, take N-phenyl-2-methylthiobenzamide, sodium acetate and acetic acid as raw material preparation [(2-phenylcarbamoylphenyl) thio] methyl acetate, yield 40%. Its reaction formula is as follows:

[0050]

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 belongs to the field of fine chemicals, and in particular relates to a method for preparing α-acyloxysulfide derivatives. Its technical points are as follows: Compound A, carboxylic acid B, sodium salt of carboxylic acid B and 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroboric acid ) salts are successively added to the sealed tube containing the reaction solvent acetonitrile for reaction, and the reaction solvent acetonitrile is evaporated to obtain α-acyloxysulfide derivatives. The preparation method of α-acyloxysulfide derivatives of the present invention follows the tenet of green chemistry, and solves the problems of high toxicity of sulfoxide in the traditional preparation of α-acyloxysulfide derivatives. At the same time, the present invention adopts The catalyst has few types of raw materials, simple catalyst reaction process, simple product purification method and high yield, and has industrial value.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a method for preparing alpha-acyloxysulfide derivatives. Background technique [0002] α-Acyloxysulfides are an important class of organic compounds, and their parent structures are widely found in different natural products. At the same time, such derivatives are also important organic synthesis intermediates, which can be used to synthesize aldehydes and ketones. Therefore, how to directly and efficiently synthesize such compounds has attracted great attention of chemists. [0003] At present, there are mainly two types of methods for the synthesis of α-acyloxysulfides. The first method uses sulfoxide compounds as raw materials and uses Pummerer rearrangement to synthesize α-acyloxysulfides. The defect of this type of method is that the sulfoxide raw materials need to be synthesized in advance. ; The second uses thioether compounds as raw materials, under the action o...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/20C07C323/62C07D213/75C07D333/38
CPCC07C319/20C07D213/75C07D333/38C07C323/62
Inventor 李正义李云剑戴胜飞杨科孙小强
Owner CHANGZHOU UNIV