Alkali-free green synthetic method for isothiocyanate

An isothiocyanate, green synthesis technology, applied in the direction of organic chemistry, etc., to achieve the effect of good application value

Active Publication Date: 2015-08-26
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But these two methods still have a drawback, that is, they all need to add a large amount of alkali (excessive)

Method used

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  • Alkali-free green synthetic method for isothiocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Phenoxythiol chloride (1 mmol), 15 ml of toluene and aniline (2 mmol) were successively added into a 50 ml one-necked flask, and heated and stirred at 115° C. for 16 h. Stop the reaction, cool down, spin dry, add 20ml of dichloromethane, then use 10% dilute hydrochloric acid to extract and separate the organic phase, wash with water, wash with saturated brine, anhydrous Na 2 SO 4 Dry and separate by column chromatography (ethyl acetate:petroleum ether=1:5) to obtain phenyl isothiocyanate with a yield of 80%.

[0026] 1 H NMR (500MHz, CDCl 3 )δ: 7.35(t, J=7.5Hz, 2H, ArH), 7.28(d, J=7.5Hz, 1H, ArH), 7.23(d, J=7.5Hz, 2H, ArH); 13 C NMR (125MHz, CDCl 3 )δ: 130.2, 128.5, 126.3, 124.7, 123.2; MS (70eV) m / z (%): 135 (M + ,100).

Embodiment 2

[0028] Referring to the method of Example 1, using p-fluorophenoxysulfonyl chloride as the carbon sulfide reagent, the yield of the target product was 78%.

Embodiment 3

[0030] Referring to the method of Example 1, the molar ratio of phenoxysulfonyl chloride to benzylamine was 1:1.2, and the yield of the target product was 61%.

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Abstract

The invention discloses an alkali-free green synthetic method for isothiocyanate, and relates to the field of organic chemical industry. The method includes the steps: (1) adding solvents into carbon sulfide reagents and primary amine serving as raw materials, performing organic reaction at the temperature of 100-150 DEG C for 10-30 hours; (2) cooling and spin-drying the raw materials after reaction, adding dichloromethane, extracting and separating organic phases by 10% of dilute hydrochloride acid, washing the organic phases, combining the organic phases into an organic layer, washing the organic layer with saturated salt water, drying the organic layer by anhydrous Na2SO4, and performing column chromatographic separation to obtain the isothiocyanate. The molar ratio of the carbon sulfide reagents to the primary amine is 1:1.2-3. Compared with a preparation method in the prior art, the method has the advantages that only heating reaction needs to be performed in the solvents, additional alkali is omitted, and the method is greener and more environmentally friendly and has better application values.

Description

technical field [0001] The invention relates to the field of organic chemical industry, in particular to an alkali-free and green method for synthesizing isothiocyanate. Background technique [0002] Isothiocyanate is a class of compounds with R-N=C=S structure, and is a class of organic synthesis intermediates and pharmaceutical intermediates with a wide range of uses. It is widely used in the preparation of medicine, pesticides and dyes. Therefore, isothiocyanate The synthesis of esters has always been an important topic in organic chemistry. [0003] Before the present invention was made, the preparation method of isothiocyanate mainly contained the following approaches: [0004] Thiophosgene synthesis method: isothiocyanate is generated by the direct reaction of thiophosgene and amine compounds, but this reaction requires the use of thiophosgene, which is a highly toxic and volatile liquid, and its production , transportation and use are not safe, and the harm to the e...

Claims

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Application Information

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IPC IPC(8): C07C331/28C07C331/24C07C331/20
Inventor 李正义张金龙石嵩郑崇谦庄跃殷乐孙小强
Owner CHANGZHOU UNIV
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