Preparation method of 2-amino-n-(2,2,2-trifluoroethyl)acetamide or salt thereof

A technology of trifluoroethylamine and chloroacetyl chloride is applied in the preparation of carboxylic acid amides, the preparation of organic compounds, chemical instruments and methods, etc. The effect of industrialized production, low production cost and simple post-processing

Pending Publication Date: 2022-02-18
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] (1) The reaction needs to be carried out under high pressure, and the conditions are harsh, which is not conducive to industrial production;
[0013] (2) Condensing agents such as CDI or DCC need to be used in the reaction, which is expensive and the production cost is high;
[0014] (3) There are many steps in the reaction operation, which is easy to produce a large amount of pollutants, which is not conducive to environmental protection
[0015] (4) The post-processing is complicated, which is not conducive to industrial production

Method used

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  • Preparation method of 2-amino-n-(2,2,2-trifluoroethyl)acetamide or salt thereof
  • Preparation method of 2-amino-n-(2,2,2-trifluoroethyl)acetamide or salt thereof
  • Preparation method of 2-amino-n-(2,2,2-trifluoroethyl)acetamide or salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: Preparation of 2-chloro-N-(2,2,2-trifluoroethyl)acetamide

[0060] Add trifluoroethylamine hydrochloride (100.00g) and water (100.00g) into the reaction flask, stir and cool down in a low-temperature tank at -5°C; add precooled 30% aqueous sodium hydroxide solution (200.00g) and dichloro Methane (300.0g); add dropwise a dichloromethane solution of chloroacetyl chloride (86.62g of chloroacetyl chloride dissolved in 100g of dichloromethane) at an internal temperature of 0-5°C, and continue the reaction at 0-5°C for 1.5h ( Sampling and measuring GC, trifluoroethylamine <0.1% indicates that the reaction is complete); transfer to room temperature, stir and heat up to a temperature above 20°C in the bottle, stand for liquid separation; take the organic phase and evaporate to dryness under reduced pressure at 40°C to obtain 2- Chloro-N-(2,2,2-trifluoroethyl)acetamide: white solid 128.23g, yield 99.00%, GC detection, purity 99.33%.

Embodiment 2

[0061] Example 2: Preparation of 2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride

[0062] Add 2-chloro-N-(2,2,2-trifluoroethyl)acetamide (120.00g) and ammonia water (960.00g) into the reaction flask, react at 40°C for 2h, take 2 drops to measure GC (2-chloro- N-(2,2,2-trifluoroethyl)acetamide <0.1% indicates complete reaction); evaporated to dryness under reduced pressure at 60-70°C to obtain 132.79g of white solid (take a sample of 3mg, add 1mL of 1mol / L sodium carbonate aqueous solution Dissolve, extract with 1.5mL dichloromethane, take the lower layer solution and measure GC, the purity is 93.26%).

[0063] Add ethyl acetate (240.00 g) to the white solid obtained by evaporation to dryness above, and beat at room temperature for 2 h; filter, rinse the filter cake with 50 g of ethyl acetate, and dry it in a vacuum oven at 50 ° C for 8 h to obtain 2-amino-N-( 2,2,2-Trifluoroethyl)acetamide hydrochloride: 118.05 g of white solid, yield 89.68%, sampling by GC, purity 99...

Embodiment 3

[0065] Example 3: Preparation of 2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride

[0066] Add 2-chloro-N-(2,2,2-trifluoroethyl)acetamide (120.00g) and ammonia water (960.00g) into the reaction flask, react at 40°C for 2h, take 2 drops to measure GC (2-chloro- N-(2,2,2-trifluoroethyl)acetamide <0.1% indicates complete reaction); evaporated to dryness under reduced pressure at 60-70°C to obtain 135.13g of white solid (take a sample of 3mg, add 1mL of 1mol / L sodium carbonate aqueous solution Dissolve, extract with 1.5mL dichloromethane, take the lower layer solution and measure GC, the purity is 92.28%);

[0067] Add 240.00 g of 20% aqueous sodium hydroxide solution (W / W) to the white solid obtained by evaporation to dryness above. After dissolving, add 840.00 g of n-butanol, add solid sodium chloride until the water phase is saturated, and stir at room temperature for 0.5 h. Separation; add 420.00 g of n-butanol to the aqueous phase, extract, and combine the organic pha...

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Abstract

The invention relates to a preparation method of 2-amino-n-(2,2,2-trifluoroethyl)acetamide or a salt thereof, belonging to the field of medicinal chemistry. The preparation method comprises the following steps: carrying out a reaction on raw materials and amine or ammonium, and carrying out post-treatment to prepare 2-amino-n-(2,2,2-trifluoroethyl)acetamide or the salt thereof. According to the preparation method provided by the invention, an obtained product is low in impurity content, reaction conditions are mild, post-treatment is simple, energy consumption is low, cost can be reduced, and industrial implementation is facilitated.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of 2-amino-N-(2,2,2-trifluoroethyl)acetamide or a salt thereof. Background technique [0002] 2-Amino-N-(2,2,2-trifluoroethyl)acetamide, which usually exists stably in the form of salt, is a key intermediate in the synthesis of a new broad-spectrum insecticidal veterinary drug fluralaner. Freilaner belongs to the isoxazoline animal insecticides, which work by interfering with γ-aminobutyric acid (GABA)-gated chloride ion channels, and interact with phenylpyrazoles, cyclopentadienes and macrolides Compared with other animal insecticides, there are significant differences in molecular structure, action site, selectivity and cross-resistance, etc., and have the characteristics of safety to mammals and high insecticidal activity. [0003] In Chinese patent CN107353222, the glycine protected by N-phthaloyl reacts with trifluoroethylamine or its salt to form an ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C231/24C07C237/06C07C231/02C07C233/13
CPCC07C231/12C07C231/02C07C231/24C07C233/13C07C237/06
Inventor 王仲清田凯寇景平孙景伟廖雅倩黄芳芳
Owner SUNSHINE LAKE PHARM CO LTD
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