917391-29-8

916975-92-3

75-75-2

917391-29-8

Example 12 Synthesis of 4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole methanesulfonate (XXIX): the crude 4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole (IX) (1.85 g, 6 mmol, HPLC purity 88 area%) was dissolved in ethyl acetate (6 mL) and the temperature was maintained at about 50 °C. Methanesulfonic acid (0.397 mL, 6 mmol) was slowly added to the stirred black solution. Upon completion of the addition, a bright solid was observed to begin precipitating. The reaction mixture was slowly cooled to room temperature and stirring was continued at about 5 °C for 75 minutes. The precipitated solid was collected by filtration, washed with ethyl acetate (4 mL) and subsequently dried at room temperature and under reduced pressure. The resulting product was suspended in 2-propanol (5 mL) and stirred at 50 °C for 90 minutes, then cooled to room temperature and continued stirring for 1 hour, and finally at 0-5 °C for another 1 hour. The solid formed was collected by filtration, washed with cold 2-propanol (5 mL) and dried at room temperature and under reduced pressure to afford 4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole methanesulfonate as a beige solid. Yield: 54.1% (HPLC purity: 99.5 area%), melting point: 208-213 °C.