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Application of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Ten (10) mL of a 36% aqueous solution of formaldehyde was added to a solution containing 1.00 g of A- trifluoromethylimidazole and 0.4 mL of a 10% tetra-n- butylammonium hydroxide solution in 10 mL of tetrahydrofuranat room temperature. The mixture was stirred at the same temperature for 14 hours and then concentrated under reduced pressure. The resultant residue was subjected to column chromatography to obtain crude 4- trifluoromethylimidazol-1-ylmethanol . The crude product was dissolved in 20 mL of chloroform and thereto 0.8 mL of thionyl chloride was added at room temperature. The mixture was stirred under reflux conditions for 16 hours, allowed to be cooled to room temperature, and then concentrated under reduced pressure. The resultant residue was dissolved in 20 mL of tetrahydrofuran and thereto 940 mg of S- (3, 3, 3-trifluoropropyl) benzenethioate was added. To the solution, 2.4 mL of a 28% solution of sodium methoxide in methanol was added dropwise at room temperature. After stirring at the same temperature for 10 hours, to the reaction mixture was added 10% hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to column chromatography to obtain 800 mg of 4-trifluoromethyl-1- [ (3, 3, 3- trifluoropropylsulfanyl) methyl] -lH-imidazole (hereinafter referred to as the present compound (3)) . The present compound (3) : 1H-NMR (CDCl3, TMS): delta (ppm) 7.65 (IH, s), 7.43 (IH, s), 5.01 (2H, s), 2.67-2.71 (2H, m) , 2.27-2.381 (2H, m) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethyl)-1H-imidazole, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/28727; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem