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Synthetic method for 2-methyl-3-trifluoromethylaniline

A technology of trifluoromethylaniline and a synthesis method, which is applied in the preparation of amino compounds, chemical instruments and methods, preparation of amino compounds from amines, etc., can solve the problems of cumbersome experimental process and poor operability, and achieves easy handling and environmental protection pressure. Small, production-safe effect

Active Publication Date: 2018-11-30
JINAN ENLIGHTEN BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The experimental process of this route is cumbersome, and the operability of industrialization is poor, so it is not suitable for development as an industrialized route. The synthetic route is as follows:

Method used

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  • Synthetic method for 2-methyl-3-trifluoromethylaniline
  • Synthetic method for 2-methyl-3-trifluoromethylaniline
  • Synthetic method for 2-methyl-3-trifluoromethylaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1, Synthesis of 6-chloro-2-(methylthio)methyl-3-trifluoromethylaniline:

[0039] Weigh 606.2g of 2-chloro-3-trifluoromethylaniline, add 4L of dichloroethane, stir evenly, add 280.2g of dimethyl sulfide, N-chlorosuccinimide to the system, and control the adding speed , so that the temperature of the system is not higher than 30 degrees, after the addition, the system is stirred at room temperature for 6 hours, then 636g of triethylamine is added to the system, the system is heated to reflux, the temperature is lowered, water is added, liquid separation, desolventization, and the residue is reduced Pressure distillation, the product 635.8g yield 80%, HPLC purity greater than 97%. 1 H NMR (600MHz, CDCl 3 )δ7.304(d, J=8.4Hz, 1H), 7.016(d, J=8.4Hz, 1H), 5.2–4.7(br s, 2H), 3.885(s, 2H), 2.051(s, 3H)

[0040] 2. Synthesis of 6-chloro-2-chloromethyl-3-trifluoromethylaniline hydrochloride:

[0041] Weigh 568.2g of 6-chloro-2-(methylthio)methyl-3-trifluoromethylaniline in a re...

Embodiment 2

[0045] 1, Synthesis of 6-chloro-2-(methylthio)methyl-3-trifluoromethylaniline:

[0046] Weigh 1170g of 2-chloro-3-trifluoromethylaniline, add 17L of dichloroethane, stir evenly, add 354g of dimethyl sulfide and 961g of N-chlorosuccinimide to the system, control the adding speed, Make the temperature of the system not higher than 30 degrees. After the addition, the system is stirred at room temperature for 6 hours, then 1214g of triethylamine is added to the system, the system is heated to reflux, the temperature is lowered, water is added, the liquid is separated, the solvent is removed, and the residue is decompressed. Distilled to obtain the product 1193g yield 78%, HPLC purity greater than 95%. 1 H NMR (600MHz, CDCl 3 )δ7.304(d, J=8.4Hz, 1H), 7.016(d, J=8.4Hz, 1H), 5.2–4.7(br s, 2H), 3.885(s, 2H), 2.051(s, 3H)

[0047] 2. Synthesis of 6-chloro-2-chloromethyl-3-trifluoromethylaniline hydrochloride:

[0048] Weigh 1020g of 6-chloro-2-(methylthio)methyl-3-trifluoromethylani...

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Abstract

The invention discloses a synthetic method for 2-methyl-3-trifluoromethylaniline. The method comprises the following steps: with 2-chloro-3-trifluoromethylaniline as a raw material, introducing a methylthio group onto the 2-chloro-3-trifluoromethylaniline, carrying out a reaction with sulfonyl chloride so as to convert the methylthio group into a chloromethyl group, and carrying out neutralizationand hydrogenation so as to obtain a pure product namely the 2-methyl-3-trifluoromethylaniline. The synthetic method provided by the invention has a synthetic route which is described in the specification. The preparation method provided by the invention adopts more economical raw materials, has simple and convenient preparation process, is free of participation of toxic substances, reaches a yield of 70%, obtains a product with a purity higher than 99%, has good economic significance, and is applicable to large-scale industrial production.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for synthesizing 2-methyl-3-trifluoromethylaniline by using 2-chloro-3-trifluoromethylaniline as a raw material. Background technique [0002] 2-Methyl-3-Trifluoromethyl Aniline (2-Methyl-3-Trifluoromethyl Aniline), is an important pharmaceutical and pesticide intermediate, mainly used in the synthesis of painkillers and herbicides, and veterinary anti-inflammatory It is also a key intermediate for the synthesis of flunixin meglumine. Due to the unique positions of the substituents on the benzene ring of 2-methyl-3-trifluoromethylaniline, the synthesis process is relatively complicated and the production cost is relatively high. The synthesis methods of 2-chloro-3-trifluoromethylaniline disclosed in the prior art all have certain disadvantages. [0003] U.S. Patent No. 5,965,735 discloses a synthetic route using m-aminobenzotrifluoride as a starting material. First, t...

Claims

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Application Information

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IPC IPC(8): C07C209/74C07C211/52
CPCC07C209/68C07C209/74C07C319/20C07C211/52C07C323/29
Inventor 李宏卫洁李新卢朋孙斌胡大伟贺军毛浙徽张凯
Owner JINAN ENLIGHTEN BIOTECH CO LTD
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