Simple exploration of 4-Methoxy-3-(trifluoromethyl)aniline

According to the analysis of related databases, 393-15-7, the application of this compound in the production field has become more and more popular.

Application of 393-15-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 393-15-7 as follows.

General procedure: 2-Bromoethyl amine (1 equiv.) and 4-Chlorphenylsulfonylchloride (1 equiv.) were dissolved in dry CH2Cl2under argon and triethyl amine (1.5 equiv) was added. The resultingreaction mixture was stirred at room temperature for 5 h. Then, waterand CH2Cl2 were added, followed by thorough extraction of theaqueous layer with CH2Cl2. The combined organic layer was driedover Na2SO4 and concentrated under reduced pressure. The residue waspurified via column chromatography (heptane/EtOAc, gradient 10:0 to1:1) to afford desired N-(2-bromoethyl)-4-chlorobenzene sulfonamideas intermediate which was dissolved in toluene (15 mL/mmol).Thereafter, a solution of KOH (3 equiv) in water (1 mL/mmol) wasadded. The resulting reaction mixture was stirred at room temperaturefor 90 min. After complete conversion, water and ethyl acetate wereadded, followed by thorough extraction of the aqueous layer withEtOAc. The combined organic layer was dried over Na2SO4 andconcentrated under reduced pressure. The residue was purified viacolumn chromatography (heptane/EtOAc, gradient) to afford desired 1-[(4-chlorophenyl)sulfonyl]aziridine as intermediate. 1-[(4-chlorophenyl)sulfonyl]aziridine (150 mg, 0.69 mmol), 4-fluoro-3-trifluoromethyl aniline (123 mg, 0.69 mmol) and SiO2 (100 mg,1.66 mmol) were then suspended in H2O (2 mL), and the resultingreaction mixture was treated with ultra sound for 90 min and wasstirred at room temperature for 20 h. Upon addition of water and ethylacetate the aqueous layer was extracted thoroughly with ethyl acetate.The combined organic layer was dried over Na2SO4 and concentratedunder reduced pressure. Purification of the remaining residue viacolumn chromatography (heptane/EtOAc, gradient) afforded N-(2-{[4-fluoro-3-(tri-fluormethyl)phenyl]amino}ethyl)-4-chlorobenzenesulfonamide

According to the analysis of related databases, 393-15-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Frackenpohl, Jens; Schneider, Linn; Decker, Luka J.B.; Dittgen, Jan; Fenkl, Franz; Fischer, Christian; Franke, Jana; Freigang, Joerg; Getachew, Rahel; Gonzalez Fernandez-Nino, Susana M.; Helmke, Hendrik; Hills, Martin J.; Hohmann, Sabine; Kleemann, Jochen; Kurowski, Karoline; Lange, Gudrun; Luemmen, Peter; Meyering, Nicole; Poree, Fabien; Schmutzler, Dirk; Wrede, Sebastian; Bioorganic and Medicinal Chemistry; vol. 27; 24; (2019);,
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