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Method for preparing N,N-diethyl-4-thiocyanatoaniline

A technology of thiocyanatoaniline and diethylaniline, which is applied in the field of preparing N,N-diethyl-4-thiocyanatoaniline, and achieves the effect of low production cost and less pollution

Inactive Publication Date: 2017-01-11
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently through the SCN - In the reaction system of synthesizing thiocyanatoaniline with the reaction of benzene ring, the use of air or oxygen as the oxidant has not been reported yet

Method used

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  • Method for preparing N,N-diethyl-4-thiocyanatoaniline
  • Method for preparing N,N-diethyl-4-thiocyanatoaniline
  • Method for preparing N,N-diethyl-4-thiocyanatoaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 0.5mmol N,N-diethylaniline, 1mmol ammonium thiocyanate, 2mL acetonitrile and 0.2mL trifluoroacetic acid (the mass fraction of trifluoroacetic acid is 100%) into the reaction tube, and then inject 0.046mmol nitrogen dioxide and Air at an atmospheric pressure, seal the reaction tube and react at 15°C for 3 hours (when the reaction tube is sealed, the air is also sealed in the reaction tube, so the reaction is carried out in the air, and the oxygen in the air plays an oxidation role). After the reaction is finished, add aqueous sodium hydroxide solution to make the pH of the reaction system 8 to 9. The N,N-diethyl-4-thiocyanatoaniline product exists in the form of salt in an acidic environment, and it is difficult to Purify, therefore need to be adjusted to alkaline; Utilize gas chromatography internal standard method to carry out quantitative analysis, productive rate is 94%, N,N-diethyl-4-thiocyanatoaniline product is separated and purified by column chromatography (f...

Embodiment 2

[0030] The trifluoroacetic acid in Example 1 was replaced with an equal volume of hydrochloric acid (the mass fraction of hydrochloric acid was 40%), and other conditions were the same as in Example 1. The yield of N,N-diethyl-4-thiocyanatoaniline product was 72%.

Embodiment 3-4

[0032] The ammonium thiocyanate in embodiment 1 is replaced with sodium thiocyanate and cuprous thiocyanate of equimolar amounts respectively, and other conditions are the same as embodiment 1. The yields of N,N-diethyl-4-thiocyanatoaniline products were 92% and 46%, respectively.

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Abstract

The invention aims at providing a method for preparing N,N-diethyl-4-thiocyanatoaniline. The method for preparing N,N-diethyl-4-thiocyanatoaniline comprises the following steps of: dissolving N,N-diethyl aniline and thiocyanate into an organic solvent to obtain a reaction solution, adding acid into the reaction solution, then leading the reaction solution to react airtightly for 0.5-5h at 0-40 DEG C in a reaction container under the action of nitrogen dioxide and air, to obtain N,N-diethyl-4-thiocyanatoaniline. According to the method, not only can the pollution be reduced, but also the production cost can be effectively lowered by using air as an oxidant.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing N,N-diethyl-4-thiocyanatoaniline. Background technique [0002] Thiocyanatoanilines are an important class of organic chemicals, which can be used as insecticides and fungicides, and can also be converted into various types of sulfur-containing compounds (R.G.Guy, The Chemistry of cyanates and their thioderivatives, John Wiley and Sons, New York, 1977). Generally, thiocyanatoaniline is synthesized by thiocyanation reaction of benzene ring [1] . The thiocyanation reagent used is (SCN) 2 [2] ,N-thiocyanosuccinimide [3] or anion for SCN - Thiocyanate [4] . Compared with the first two thiocyanating reagents, thiocyanate is more common and easy to obtain, and is widely used in actual production. But SCN - It is an electrophile and cannot directly react with the benzene ring; therefore, an oxidizing agent needs to be added in the r...

Claims

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Application Information

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IPC IPC(8): C07C331/12
CPCC07C331/12
Inventor 任运来赵博田欣哲王文会申振鹏
Owner HENAN UNIV OF SCI & TECH