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Method for synthesizing isorhodanate

A technology of isothiocyanate and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of difficulty in synthesis and purification of isocyanide, unfavorable industrialized large-scale production, etc., achieve great implementation value, social and economic benefits, and low production cost , the advanced effect of the process route

Inactive Publication Date: 2006-12-20
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis and purification of isonitrile is very difficult, and it is also a highly toxic substance, which has many factors that are not conducive to industrial production

Method used

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  • Method for synthesizing isorhodanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1——the synthesis of p-nitrophenylisothiocyanate

[0023] In a 1000ml four-neck flask equipped with mechanical stirring, a dry constant pressure dropping funnel, a reflux condenser and a thermometer, add 1mol p-nitroaniline, 1mol triethylamine and 450ml tetrahydrofuran under nitrogen protection, start stirring, and At -10°C, slowly add carbon disulfide solution dissolved in 100 ml of tetrahydrofuran dropwise. After the addition and stirring for 5 hours, a large amount of solids precipitated, filtered with suction, and washed with a small amount of tetrahydrofuran. After drying, p-nitrobenzene dithioformate is obtained, and after recrystallization with solvents such as toluene, benzene, ethanol, methanol, ether, etc., high-purity p-nitrobenzene dithioformate is obtained.

[0024] Then above-mentioned 0.5mol of p-nitrobenzene dithioformate and a small amount of catalyst triethylamine are dissolved in 250ml of dichloromethane, and the dichloromethane solution tha...

Embodiment 2

[0025] Embodiment 2——the synthesis of p-chlorophenylisothiocyanate

[0026] In the 1000ml four-neck flask equipped with mechanical stirring, dry constant pressure dropping funnel, reflux condenser and thermometer, add 1mol p-chloroaniline, 1mol triethylenediamine 450ml dichloromethane under nitrogen protection, start stirring, and At 0-10°C, slowly add carbon disulfide solution dissolved in 100ml of dichloromethane dropwise. After adding and stirring for 5 hours, a large amount of solids precipitated, filtered with suction, and washed with a small amount of dichloromethane. After drying, p-chlorobenzenedithioformate was obtained.

[0027] Then above-mentioned 0.5mol of p-chlorobenzenedithioformate and a small amount of catalyst triethylamine were dissolved in 250ml of dichloromethane, and the dichloromethane solution of methylphenyldichlorosilane was slowly added dropwise. After adding, Slowly warm up to room temperature, then heat to reflux for 3-5 hours. After the reaction...

Embodiment 3

[0028] Embodiment 3——the synthesis of p-acetylphenylisothiocyanate

[0029] In a 1000ml four-neck flask equipped with mechanical stirring, a dry constant pressure dropping funnel, a reflux condenser and a thermometer, add 1mol p-acetylaniline, 1mol triethylenediamine, 450ml chloroform under nitrogen protection, and start stirring. Slowly add carbon disulfide solution dissolved in 100ml of dichloromethane dropwise at 0-10°C. After adding and stirring for 5 hours, a large amount of solids precipitated, filtered with suction, and washed with a small amount of chloroform. After drying, p-chlorobenzenedithioformate was obtained.

[0030] Then 0.5mol of the above-mentioned p-chlorobenzenedithioformate and a small amount of catalyst triethylamine were dissolved in 250ml of dichloromethane, and the dichloromethane solution of dimethyldichlorosilane was slowly added dropwise. The temperature was raised to room temperature, and then heated to reflux for 3-5 hours. After the reaction w...

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Abstract

This invention relates to a method for synthesizing isosulfocyanate, characterizing of rational process, environmental friendly, safe and reliable production, high recovering rate, and basically no three wastes. The procedures comprise: dissolve the raw material aminated compounds and carbon bisulphide in organic solvent to synthesize dithiocarbamate under alkaline action, and then react with chloro-silicane to synthesize isosulfocyanate under catalyst action, wherein it employs two-step method for low activity aminated compound and one-step method for high activity aminated compound.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for synthesizing isothiocyanates. Background technique [0002] Isothiocyanate is an important organic synthetic intermediate for the synthesis of heterocyclic compounds containing both sulfur and nitrogen atoms, and is also an important starting material for the synthesis of pesticides with antifungal activity and insect repellent effects. Faulkner found that some isothiocyanates, such as phenylethyl isothiocyanate (PEITC), not only have anticancer activity but also inhibit enzymes of HIV. With the research on marine organisms in recent years, a large number of isothiocyanates have been separated, such as half bernesene isothiocyanate, etc., which has promoted the research and development of isothiocyanates in many research institutions. . [0003] Before the present invention was made, the chemical method of existing synthetic isothiocyanate mainly contained followin...

Claims

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Application Information

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IPC IPC(8): C07C331/16
Inventor 边高峰来国桥邱化玉胡自强齐凡
Owner HANGZHOU NORMAL UNIVERSITY
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