* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
nitrophenyl trifluoromethyl ether Using the same reactor setup as in Example 1, the reactor is charged with 3-nitrophenol (13.9 g, 0.1 mol), anhydrous carbon tetrachloride (38 ml, 0.39 mol), anhydrous antimony trifluoride (53.6 g, 0.3 mol) and a catalytic amount of antimony pentachloride (1 ml, 7.7 mmol). The reactor is then sealed and heated at 150 C (internal) with vigorous stirring for 5.5 hours. Subsequently, the reactor is opened and the contents neutralized with saturated NaHC03 The product is separated by steam distillation, and a 62 percent yield of the product is obtained.
nitrophenyl trifluoromethyl ether A 300 cc Parr reactor (steel) equipped with a sealed mechanical stirrer and an internal thermocouple is dried, flushed with nitrogen and charged with 4-nitrophenol (1.4 g, 10 mmol), anhydrous carbon tetrachloride (4 ml, 41.4 mmol), anhydrous antimony trifluoride (5.5 g, 30.8 mmol), and a catalytic amount of antimony pentachloride (0.1 ml, 0.77 mmol). The reactor is then sealed and heated at 150 C (internal) with vigorous stirring for 6.5 hours. Subsequently, the reaction vessel is opened and the contents partitioned between ether and saturated NaHCO3. Concentration of the organic extract, and flash chromatography of the concentrate produces a 29 percent yield of the desired product.
Intermediate 22: Step a3-Nitro-4-trifluoromethoxy-benzenesulfonamide To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid.
Intermediate 30: Step a 3-Nitro-4-trifluoromethoxy-benzenesulfonamide To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid.
Intermediate 62: Step a 3-Nitro-4-trifluoromethoxy-benzenesulfonamide To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid.
To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid.
To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid.
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