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Method for preparing isothiocyanate

A technology of isothiocyanate and acid-binding agent, which is applied in the field of preparation of isothiocyanate, can solve the problems of inconvenient acquisition of formamide and sulfonyl halide, low yield of target product, cumbersome operation process, etc., and achieve separation The effect of convenient purification, short reaction time, and easy availability of reaction raw materials

Inactive Publication Date: 2012-06-20
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many defects in this method: the yield of the target product is low, the operation process is cumbersome, and the amount of solvent is large
However, the acquisition of formamide and sulfonyl halide is still inconvenient and uneconomical

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Weigh phenoxysulfonyl chloride (1 mmol) and sodium hydroxide (1 mmol), respectively, into a single-necked flask filled with dichloromethane (5 mL), at -30 0 Stir at C. Benzylamine (1 mmol) was then weighed and dissolved in dichloromethane (1 mL), added dropwise into the above flask, and stirred for 30 hours. Stop the reaction, add water (10 mL) and dichloromethane (15 mL), extract and separate the organic phase, then extract the water phase with dichloromethane (15 mL), combine the organic phases, wash with saturated brine (15 mL), Dry over anhydrous sodium sulfate. After separation by column chromatography (ethyl acetate:petroleum ether = 1:5), benzyl isothiocyanate was obtained with a yield of 80%.

[0025] 1 H NMR (500 MHz, CDCl 3 ) δ : 7.39 (t, J = 7.0 Hz, 2H, ArH), 7.35 (d, J = 7.0 Hz, 1H, ArH), 7.31 (d, J = 7.0 Hz, 2H, ArH), 4.71 (s, 2H, NCH 2 ). 13 C NMR (125 MHz, CDCl 3 ) δ : 134.3, 129.0 (N=C=S), 128.4, 126.8, 48.7. GCMS m / z 149.

Embodiment 2

[0027] Weigh phenoxysulfonyl chloride (3 mmol) and sodium hydroxide (10 mmol), add them to a single-necked flask filled with xylene (5 mL), and stir at room temperature. Then weigh benzylamine (1 mmol) and dissolve it in xylene (1 mL), add it dropwise to the above flask, after the addition is completed, the 0 The reaction was stirred at C for 1 hour. Stop the reaction, distill off the solvent under reduced pressure, then add water (10 mL) and dichloromethane (15 mL), extract and separate the organic phase, extract the aqueous phase with dichloromethane (15 mL), combine the organic phases, wash with saturated salt Washed with water (15 mL), dried over anhydrous sodium sulfate. After separation by column chromatography (ethyl acetate:petroleum ether = 1:5), benzyl isothiocyanate was obtained with a yield of 86%.

Embodiment 3

[0029] Weigh phenoxysulfonyl chloride (1.2 mmol) and sodium hydroxide (3 mmol), respectively add to a one-necked flask containing dichloromethane (5 mL), and stir in an ice bath. Then weigh benzylamine (1 mmol) and dissolve it in dichloromethane (1 mL), add it dropwise to the above flask, keep the temperature at 0~5°C; remove the ice bath after 1 hour, +30 0 The reaction was stirred at C for 10 hours. Stop the reaction, add water (10 mL) and dichloromethane (15 mL), extract and separate the organic phase, then extract the water phase with dichloromethane (15 mL), combine the organic phases, wash with saturated brine (15 mL), Dry over anhydrous sodium sulfate. After separation by column chromatography (ethyl acetate:petroleum ether = 1:5), benzyl isothiocyanate was obtained with a yield of 95%.

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PUM

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Abstract

The invention relates to a method for synthesizing isothiocyanate, belonging to the field of organic chemical industry. The method comprises the following steps: (1) synthesizing the isothiocyanate from a carbon sulfide reagent and primary amine used as raw materials, adding an alkali reagent used as the catalyst and the acid binding agent, and adding a solvent at the same time, wherein the organic reaction temperature is controlled at 300 DEG C below zero to 1,200 DEG C above zero, the reaction lasts for 1-30 hours, the molar ratio of the substituted phenoxy sulfuryl chloride to the alkyl primary amine is 1-3:1, and the molar ratio of the alkali reagent to the alkyl primary amine is 1-10:1; and (2) adding water and dichloromethane solution at the volume ratio of 2:3, extracting and separating organic phases, extracting the water phases by using dichloromethane, merging the organic phases, washing by using saturated salt water, drying by using nhydrous sodium sulfate, and separating by adopting chromatography to obtain the isothiocyanate. The method for synthesizing the isothiocyanate has the advantages of readily available reaction materials, low toxicity, mild reaction condition, short reaction time and convenience of separation and purification, thereby having high application value.

Description

technical field [0001] The invention relates to the field of organic chemical industry, in particular to a method for preparing isothiocyanate. Background technique [0002] Isothiocyanate is a class of organic synthesis intermediates and pharmaceutical intermediates with a wide range of uses. It is widely used in the preparation of medicines, pesticides, and dyes. Therefore, it plays an important role in both organic synthesis and chemical industry. , the research on the synthetic method of isothiocyanate 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: direct reaction of thiophosgene and amine compounds to generate isothiocyanate (T. R. Jr. Burke, B. S. Bajwa, A. E. Jacobson, K. C. Rice, R. A. Streaty, W. A. ​​Klee, J. Med. Chem. 1984, 27 , 1570-1574; Dictionary of Organic Synthesis , 1992, ...

Claims

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Application Information

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IPC IPC(8): C07C331/24C07C331/28C07C331/20C07C331/26
Inventor 李正义马鸿钊陈新刘平张卫红
Owner CHANGZHOU UNIV
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