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Preparation method of trifluoromethylamine

A technology of trifluoromethyl aromatic amines and trifluoromethylation, which is applied in the preparation of organic compounds, the preparation of amino hydroxyl compounds, the preparation of amino compounds from amines, etc., can solve the problems of not being suitable for industrial production and high synthesis costs, and achieve Conducive to large-scale industrial production, low cost of raw materials, and the effect of reducing production costs

Active Publication Date: 2018-09-07
TETRANOV PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a preparation method of trifluoromethyl aromatic amine, so as to solve the problems that the existing method has high synthesis cost and is not suitable for industrialized production

Method used

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  • Preparation method of trifluoromethylamine
  • Preparation method of trifluoromethylamine
  • Preparation method of trifluoromethylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation method of the trifluoromethyl aromatic amine of the present embodiment adopts the following steps:

[0025] 1) Weigh aniline (0.25mmol, 1.0eq), 1-trifluoromethyl-1,2-phenyliodide-3(H)-one (0.3mmol, 1.2eq), base (potassium carbonate, 0.75mmol, 3.0eq) and nickel compounds (NiCl 2 ·6H 2 O, the molar weight is 10% (10 mol%) of the molar weight of 1-trifluoromethyl-1,2-phenyliodyl-3(H)-one) in a reaction tube, add 2 mL of dioxane as a solvent , Under the protection of argon, heated to 80 ° C and stirred for 12 h.

[0026] 2) The reaction solution obtained after the reaction was cooled to room temperature, and the reaction solution was diluted with 10 mL of dichloromethane, filtered, and the solid was washed with 5 mL of dichloromethane, and the washing liquid was merged into the filtrate, and then the filtrate was washed twice with water (each time consumption 10mL), the organic phase after extraction is dried with anhydrous sodium sulfate, filtered, and t...

Embodiment 2-27

[0028] The preparation process parameters of the trifluoromethyl aromatic amines of Examples 2-27 are shown in Table 1.

[0029] The preparation process parameter of the trifluoromethyl aromatic amine of table 1 embodiment 2-27

[0030]

[0031]

[0032] The reaction process of embodiment 1-27 is as follows:

[0033]

[0034] The yield listed in Table 1 is the total yield of products 3a and 4a, which is determined by gas chromatography with dipentyl phthalate as the internal standard.

[0035] The yield of embodiment 1 is 38%, and the reaction of embodiment 2-7, only the kind of nickel compound is different, and other is identical with embodiment 1, as can be seen, the yield with nickel hydroxide as catalyzer is the highest.

Embodiment 8

[0036] In embodiment 8, the addition of nickel hydroxide is 5mol% (in terms of the molar weight of 1-trifluoromethyl-1,2-phenyliodyl-3(H)-ketone), and other conditions are the same as in embodiment 1 .

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Abstract

The invention relates to a preparation method of trifluoromethylamine. The method includes the following steps that aromatic amine shown in the formula (1) and a trifluoromethyl reagent shown in the formula (2) react in a solvent under the condition that an alkali and / or nickel compound exists, and the trifluoromethylamine compound shown in the formula (3) is generated. According to the preparation method of trifluoromethylamine, aromatic amine and 1-trifluoromethyl-1,2-iodobenzoyl-3(H)-ketone serve as raw materials and react under the condition that the alkali and / or nickel compound exists through the amino positioning effect on aromatic nucleus. The synthesis steps of the method are simple, the cost of the raw materials is low, the production cost of trifluoromethylamine can be greatly reduced, and large-scale industrialized production is promoted.

Description

technical field [0001] The invention belongs to the field of synthesis of trifluoromethyl aromatic amines, in particular to a preparation method of trifluoromethyl aromatic amines. Background technique [0002] With the rapid development of fluorine chemistry, fluorine-containing compounds have shown broad development prospects and strong vitality in the fields of chemical materials, pesticides, and medicine. Very wide practical value and economic value. The introduction of fluorine atom or trifluoromethyl group can significantly improve the biological activity of the drug. At the same time, due to the strong electronegativity of the fluorine atom, the C-F bond energy is large and relatively stable, which not only enhances the stability of the drug, but also increases the stability of the drug. The fat solubility of the drug is improved, so as to achieve special effects such as good drug effect, small dosage and small side effects. Such as fluoxetine hydrochloride, mabuter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C217/84C07C209/68C07C213/08C07C255/58C07C253/30C07C229/60C07C227/16C07C225/22C07C221/00C07F5/04C07F5/02C07C317/36C07C315/04
CPCC07C209/68C07C213/08C07C221/00C07C227/16C07C253/30C07C315/04C07F5/025C07F5/04C07C211/52C07C217/84C07C255/58C07C229/60C07C225/22C07C317/36
Inventor 吴豫生高献英耿阳韩帅军梁阿朋李敬亚邹大鹏吴养洁
Owner TETRANOV PHARMA CO LTD
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