Synthesis method of 4-methanesulfonylbutyl isothiocyanate

A technology of methanesulfonylbutyl isothiocyanate and a synthesis method, which is applied in the field of chemical synthesis of 4-methanesulfonylbutyl isothiocyanate, can solve problems such as high cost of anhydrous sodium methanethiolate, and achieve cost reduction, The effect of reduced overall yield and simple synthesis steps

Active Publication Date: 2017-03-15
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this process is that the intermediate product of each step must be separated and purified, and the cost of anhydrous sodium methyl mercaptide is very expensive, and the batch production of this raw material cannot be carried out in China

Method used

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  • Synthesis method of 4-methanesulfonylbutyl isothiocyanate
  • Synthesis method of 4-methanesulfonylbutyl isothiocyanate
  • Synthesis method of 4-methanesulfonylbutyl isothiocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Dissolve 3.53g (20.6mmol) of 1-bromo-4-chlorobutane in 50ml of anhydrous DMF, add to a 250ml round-bottomed flask, stir in an ice bath at 0°C, and slowly drop in the solution containing 3.03g (21.63mmol, 1.05 times the amount) of 50% sodium methyl mercaptan in absolute ethanol was naturally warmed to room temperature and left overnight. The total reaction time was 20h. Stirring was stopped, and the ethanol was removed by rotary evaporation at low temperature in vacuum, extracted three times continuously with n-hexane, washed with saturated sodium chloride successively, dried the extract with anhydrous sodium sulfate, and filtered off the insoluble matter. The n-hexane was removed by low-temperature rotary evaporation under vacuum to obtain 2.30 g of a colorless oily substance with a strong mustard smell. The intermediate content was determined to be about 78.8% by GC-MS, and the yield of intermediate I was about 63.3%. Mass spectral data (GC-MS, EI): 138.1, 103.1, 9...

Embodiment 2

[0055] (1) Dissolve 3.53g (20.6mmol) of 1-bromo-4-chlorobutane in 50ml of absolute ethanol, add to a 250ml round-bottomed flask, stir in an ice bath at 0°C, and slowly drop in the solution containing 3. 11 g (22.2 mmol, 1.08 times the amount) of 50% sodium methyl mercaptide in absolute ethanol was naturally warmed to room temperature and left overnight. The total reaction time was 26 hours. Stirring was stopped, and the ethanol was removed by rotary evaporation at low temperature in vacuum, extracted three times continuously with n-hexane, washed with saturated sodium chloride successively, dried the extract with anhydrous sodium sulfate, and filtered off the insoluble matter. The n-hexane was removed by low-temperature rotary evaporation under vacuum to obtain 2.69 g of a colorless oily substance with a strong mustard smell. The intermediate content was determined to be about 81% by GC-MS, and the yield of intermediate I was about 76.3%. Spectrum data is with embodiment 1.

...

Embodiment 3

[0061] (1) Dissolve 3.53g (20.6mmol) of 1-bromo-4-chlorobutane in 50ml of absolute ethanol, add to a 250ml round-bottomed flask, stir in an ice bath at 0°C, and slowly drop in the solution containing 3.47g (24.72mmol, 1.2 times the amount) of 50% sodium methyl mercaptide in absolute ethanol was naturally warmed to room temperature, overnight, and the total reaction time was 24h. Stirring was stopped, and the ethanol was removed by rotary evaporation at low temperature in vacuum, extracted three times continuously with n-hexane, washed with saturated sodium chloride successively, dried the extract with anhydrous sodium sulfate, and filtered off the insoluble matter. The n-hexane was removed by low-temperature rotary evaporation under vacuum to obtain 2.22 g of a colorless oily substance with a strong mustard smell. The intermediate content was determined to be about 57.6% by GC-MS, and the yield of intermediate I was about 44.8%. Spectrum data is with embodiment 1.

[0062] (2...

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Abstract

The invention relates to a chemical synthesis method of 4-methanesulfonylbutyl isothiocyanate (Erysolin). The method comprises that 1-bromo-4-chlorobutane and hydrous sodium methyl mercaptide as starting raw materials undergo a reaction to produce chlorothioether, the chlorothioether and phthalimide potassium salt undergo a reaction to produce a tertiary amine conjugate, the tertiary amine conjugate undergoes a hydrazinolysis reaction to produce thioether primary amine, the thioether primary amine forms isothiocyanate under action of thiophosgene, and the isothiocyanate is oxidized to form Erysolin. The chemical synthesis method is simple in operation, uses a small amount of dangerous reagents, gives consideration to a cost and a yield and is suitable for Erysolin industrial production.

Description

technical field [0001] The present invention relates to a kind of chemical synthesis method of 4-methanesulfonyl butyl isothiocyanate (Erysolin), especially relate to a kind of 4-butane with 1-bromo-4-chlorobutane, aqueous sodium methyl mercaptide as initial raw material Synthetic method of methanesulfonyl butyl isothiocyanate. Background technique [0002] Erysolin, also known as 4-methylsulfonyl butyl isothiocyanate, is named because it comes from the genus Erysimum of the Brassicaceae. Its molecular formula is C 6 h 11 NO 2 S 2 , the relative molecular mass is 193.29, white to light lemon-colored crystals, and its structural formula is as follows: [0003] [0004] Studies have found that isothiocyanate has good anti-tumor and anti-nerve damage effects, and this type of compound is mainly derived from the cruciferous plant Saccharomyces genus. ERY plays a unique role in anti-tumor, especially for tumor cells with multi-drug resistance to chemotherapy drugs and P5...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C331/20
CPCC07C331/20
Inventor 孙立新李炳龙周慧
Owner SHENYANG PHARMA UNIVERSITY
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