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Preparation method of isothiocyanate

A technology of elemental sulfur and compounds, applied in the direction of organic chemistry, can solve the problems of unsafe production, storage, transportation and use, great environmental hazards, and low yield of target substances, and achieve easy large-scale commercial preparation and simple preparation process , Environmentally friendly effect

Inactive Publication Date: 2010-06-30
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main defect of this method is: need to use thiophosgene, and thiophosgene is a highly toxic volatile liquid, its production, storage and use are not safe, and it is also more harmful to the environment
The disadvantages of this method are: the target yield is low, the operation process is complicated, and the amount of solvent is large

Method used

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  • Preparation method of isothiocyanate
  • Preparation method of isothiocyanate
  • Preparation method of isothiocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 1-naphthalene isothiocyanate:

[0031] Add 1-naphthylcarboxamide (0.5mmol), benzenesulfonyl chloride (0.5mmol), triethylamine (1.5mmol), sulfur (0.5mmol), and 5ml of polar solvent [alkane halide (such as CH 2 Cl 2 ) or alkyl substituted benzene, etc.], heated to reflux, and tracked the reaction with thin layer chromatography (TLC). The reaction was stopped when the raw material point disappeared, and the crude product was purified through a silica gel column with petroleum ether and ethyl acetate as eluents to obtain pure 1-naphthalene isothiocyanate with a melting point of 55.3°C. The yield was 86%.

Embodiment 2～12

[0033] Using different raw materials (reactants), referring to the method of Example 1, different target objects can be obtained, see Table 1 for details.

[0034]

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PUM

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Abstract

The invention relates to a preparation method of isothiocyanate, which comprises the main step that in the presence of elemental sulfur and a catalyst, replaced formamide reacts with aryl sulfonyl halide at the temperature of 30 to 100 DEG C to obtain a target compound. The invention avoids using (thio) phosgene, derivatives (such as triphosgene) thereof and carbon disulfide, is operated safely and is environment-friendly. In addition, the synthetic route of the preparation method is simple (only one step of reaction), the preparation condition is mild, and with the method, the scale commercial preparation of the isothiocyanate is easy.

Description

technical field [0001] The present invention relates to a kind of preparation method of isothiocyanate. Background technique [0002] Isothiocyanate is an important class of organic synthesis intermediates and pharmaceutical intermediates, widely used in the preparation of organic synthesis products such as pesticides, medicines, and dyes. [0003] The synthetic method of existing isothiocyanate mainly contains: thiophosgene synthetic method, promptly makes phenyl isothiocyanate (organic synthesis classics, 1992,766, 926). The main defect of this method is: need to use thiophosgene, and thiophosgene is highly toxic volatile liquid, its production, storage and use are unsafe, and the harm to environment is also bigger. [0004] The carbon disulfide method, that is, the substituted aniline compound first reacts with carbon disulfide and an organic base to form a dithiocarbamate, and then reacts with methyl chloroformate to obtain the target (Chemical Times, 2006, 20 (3), 71~...

Claims

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Application Information

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IPC IPC(8): C07C311/16C07D239/42
Inventor 李治王玉娟杨向民章卫东
Owner EAST CHINA UNIV OF SCI & TECH
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