Method for preparing N,N-Dimethylaniline compound through alkylation of alkyl tosylate

Abstract

The invention provides a method for preparing a N,N-Dimethylaniline compound through alkylation of alkyl tosylate, and belongs to the technical field of organic synthesis. According to the method, paratoluensulfonyl chloride and fatty alcohol serve as raw materials, pyridine serves as an acid-binding agent, and the alkyl tosylate is generated; the alkyl tosylate as an alkylation reagent and an aniline compound are alkylated under the alkaline condition to obtain the N,N-Dimethylaniline compound. The method is implemented at normal pressure, the operation is simple, no waste acid is generated,the yield and the purity are high, and the method is suitable for industrial and scaled production.

Description

technical field [0001] The invention relates to a method for performing N,N-dialkylation reaction on aniline compounds by using alkyl p-toluenesulfonate as an alkylating agent, which belongs to the technical field of organic synthesis. Background technique [0002] The chemical formula of N,N-dialkylaniline compounds is as shown in S-1. [0003] [0004] N,N-dialkylaniline compounds play an important role in organic synthesis, dyes, medicine and other fields. [0005] At present, the methods for synthesizing N-alkylaniline compounds and N,N-dialkylaniline compounds mainly contain the following types: [0006] 1) Substituted alkylation method using halogenated hydrocarbon as alkylating agent: Meng Yanqiu [1] The people such as mention a kind of with o-ethylaniline and 1-bromobutane as raw material, select triethylbenzyl ammonium chloride as phase transfer catalyst, prepare the method for N,N-dibutyl o-ethylaniline, such as formula S -2 shown. Srivastava [2] 、Monopoli ...

AI Technical Summary

Problems solved by technology

[0016] S-2 uses halogenated hydrocarbons as the alkylation reagent, which is expensive. If the yield is increased, its proportion must be increased, which makes the production cost of the product higher. At the same time, industrial wastewater contains a large amount of bromide ions to pollute the environment. , if it is recycled, the relatively high cost limits the industrial development of this method

[0017] S-3 uses alcohol as an alkylating agent. Although the cost is low, alcohol is a weak electrophile, and the ability to leave alcoholic hydroxyl groups is low, and the alkylation reaction carried out by alcohol is reversible, so the reaction ability is weak and the yield is low. The efficiency is not ideal; the liquid phase method will use inorganic acid as a catalyst, which will seriously corrode the equipment; the gas phase method, the boiling point of the raw material should not be too high, is not suitable for all reactions

[0018] S-4 and S-5 use alkyl esters as alkylating reagents with high reactivity, but high toxicity, so the requirements for equipment and personal protection in actual industrialization are also very high, and the cost is very expensive; they need to be used under high temperature and high pressure It is difficult to carry out; using alkyl phosphate as an alkylating agent, the wastewater contains a large amount of phosphorus, which pollutes the environment

Images