Method for synthesizing trifluoromethyl amine

The technology of a trifluoromethyl-substituted amine and a synthetic method, which is applied in the field of preparation of trifluoromethyl-containing compounds, can solve the problems of cumbersome steps, high yield, expensive fluorocarbon nitrile, etc., and achieve short process flow and high yield , the effect of easy product

Active Publication Date: 2013-01-16
JUHUA GRP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage is that the raw material fluorocarbon nitrile is relatively expensive and not suitable for large-scale industrial production
The disadvantage is that the product obtained by this method exists in the form of hydrochloride, which needs to be purified under alkaline conditions, and the post-treatment is more complicated
[0006] 3) Hexafluoroacetone reacts with chiral benzylamine to produce N-(1,1,1-trif

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Put 1 mole of D-alanine and 12 moles of anhydrous hydrofluoric acid into a 1L stainless steel (316L material) autoclave, stir for 15 minutes, add 2.2 moles of sulfur tetrafluoride, and react at 85°C for 4 hours. After the reaction, the temperature was lowered to room temperature, the by-product thionyl fluoride and unreacted sulfur tetrafluoride were absorbed with lye, the reaction solution was poured into ice water, neutralized to alkaline with sodium hydroxide, and then extracted with dichloromethane. The extract was separated by distillation to obtain 0.86 moles of the product (S)-trifluoroisopropylamine, with a content of 99%, and a yield of 86% based on D-alanine.

Embodiment 2

[0031] The reaction device and operation steps are the same as those in Example 1, except that 1 mole of D-alanine, 3 moles of anhydrous hydrofluoric acid, and 3.2 moles of sulfur tetrafluoride are added, and the reaction is carried out at 85° C. for 3.5 hours. 0.65 mol of (S)-trifluoroisopropylamine was obtained, with a content of 97.8%, and a yield of 65% based on D-alanine.

Embodiment 3

[0033] The reaction device and operation steps are the same as those in Example 1, except that 1 mole of D-alanine, 20 moles of anhydrous hydrofluoric acid, and 1.8 moles of sulfur tetrafluoride are added, and the reaction is carried out at 85° C. for 10 h. 0.76 moles of (S)-trifluoroisopropylamine were obtained, with a content of 98.8%, and a yield of 76% based on D-alanine.

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PUM

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Abstract

The invention discloses a method for synthesizing trifluoromethyl amine. The method comprises the following steps of: mixing amino acid, anhydrous hydrofluoric acid and sulfur tetrafluoride in a molar ratio of 1:(3-20):(1.8-3.2), and reacting at temperature of between 50 and 150 DEG C for 2 to 10 hours; and cooling, neutralizing, extracting and rectifying to obtain a trifluoromethyl amine product. According to the method, a process is short; and the product is easy to separate, high in yield and stable in quality, the highest yield is 88 percent, and the content of the product is over 97.5 percent.

Description

technical field [0001] The invention relates to the technical field of fluorine fine chemical industry, in particular to the preparation of trifluoromethyl-containing compounds. Background technique [0002] Trifluoromethyl amine compounds are important intermediates in organic synthesis, mainly used in organic synthesis, pharmaceutical and pesticide intermediates, and also intermediates in liquid crystal synthesis. [0003] The method for preparing trifluoromethyl amine mainly contains the following: [0004] 1) Platinum-catalyzed hydrogenation of fluorocarbonnitriles produces 1,1-dihydroalkylamines. For example, use this method to convert CF 3 CN reduction to CF 3 CH 2 NH 2 , the yield was 80%. The disadvantage is that the raw material fluorocarbon nitrile is relatively expensive and is not suitable for large-scale industrial production. [0005] 2) Ammonolysis of halogens other than fluorine in trifluoromethyl-containing compounds with ammonia to generate trifluoro...

Claims

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Application Information

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IPC IPC(8): C07B39/00C07C209/74C07C211/15C07D209/16
Inventor 耿为利周强王树华顾永红
Owner JUHUA GRP
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