N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarboxamide

N- [4- cyano-3- (trifluoromethyl) phenyl] -2-methyl-acrylamide, 50.8 g (0.2 mol), phthalic anhydride, 47.3 g (0.32 mol ) was added to 350 ml of 1, 2-dichloroethane was added dropwise 23.1 g (0.34mol) 50percent hydrogen peroxide, the dropwise addition, the reaction incubated at 35 ~ 40 , HPLC in the control feed N- [4- cyano - 3- (trifluoromethyl) phenyl] methyl-2-acrylamide content of less than 0.5percent completion of the reaction, 1, 2-dichloroethane was distilled off under reduced pressure to give a crude product after completion of the reaction, the crude product was added to after stirring well 300 g of water, 26 g of sodium carbonate was added 13 g of sodium sulfate and 0.5 hours, filtered, washed with 50 g of water sufficient to give the finished product after drying 55 N- [4- cyano-3- (trifluoromethyl yl) phenyl] -2, 3-epoxy-2-methylpropionamide 49 g, yield 90.7percent.General procedure: To a stirred solution of the different intermediate 12-16 (3 mmol) in DCM (7 mL) was added 30percent hydrogen peroxide (3.6 mL, 32.03 mmol). The reaction mixture was put in a water bath at r.t. and trifluoroacetic anhydride (3.7 mL, 26.7 mmol) was added slowly to the mixture, which was then stirred for 24 h. The reaction mixture was transferred to a separating funnel using DCM (30 mL). The organic layer waswashed with distilled water (20 mL), sat. aq. Na2S2O3 (4x20 mL), sat. aq. NaHCO3 (3x20 mL) and brine (20 mL), dried over Na2SO4 and concentrated at reduced pressure. The data are in accordance with literature data. Obtained in 86percent yield as a yellowsolid. 1H-NMR (CDCl3): 8.38 (bs, 1H), 8.00 (d, J= 2.1 Hz, 1H), 7.88 (dd, J= 8.5 Hz, 2.1 Hz, 1H), 7.78 (d, J= 8.5 Hz, 1H), 3.00 (s, 2H), 1.68 (s, 3H).N- (4-CYANO-3-TRIFLUOROMETHYLPHENYL)-2-METHYLPROPENAMIDE (10.2 g, 40 mmol) and maleic anhydride (7.8 g, 80 mmol) were dissolved in ethyl acetate (100 mL). The UHP complex (15.1 g, 160 mmol) was added to this solution, and the mixture was stirred at room temperature for 72 hours. Subsequently, the reaction mixture was neutralized with a solution of NAOH (6.4 g, 160 mmol) in water (25 mL). After the phases separated, the organic phase was washed first with a solution of Na2SO3 (LG) in water, followed by washing with water. The solvent was evaporated, affording the crude product (10.3 g), which was crystallized from isopropanol to give pure N- (4-CYANO-3- TRIFLUOROMETHYLPHENYL) -2, 3-EPOXY-2-METHYLPROPANAMIDE ; YIELD: 8.1 g (75percent).N- (4-CYANO-3-TRIFLUOROMETHYLPHENYL)-2-METHYLPROPENAMIDE (10.2 g, 40.1 mmol) and phthalic anhydride (10.2 g, 80.3 mmol) were dissolved in ethyl acetate (100 mL). The UHP complex (15.0 g, 159 mmol) was added to this solution, and the mixture was stirred at room temperature for 72 hours. Subsequently, a solution of NAOH (6.4 g, 160 mmol) in water (25 mL) was added to the reaction mixture. After the phases separated, the organic phase was washed first with a solution of Na2SO3 (1G) in water (25 mL), and then with water. The solvent was evaporated, resulting in the crude product (10.2 g), which was crystallized from isopropanol to give pure N- (4-CYANO-3-TRIFLUOROMETHYLPHENYL) -2, 3-EPOXY-2- methylpropanamide (7.9 g; 73percent); m. p. 90-92C ; IR (KBr): 3348, 3081, 2933, 2228, 1707, 1618, 1592, 1531, 1327, 1148, 906, 849, 748, 560 cm-1.General procedure: To a solution of N-arylmethacrylamides (13a or 13b, 1.7 mmol) in CH10 ml of 30percent aqueous hydrogen peroxide is heated to 35-40° C. 20 ml of acetic anhydride is added dropwise under cooling, so that the temperature does not exceed 40-50° C. 0.02 g of wolframic acid is added and the reaction mixture is stirred for 0.5 hours at 50-55° C. 3 grams of the amide (7) is added to the mixture portionwise and the reaction mixture is stirred for 6 hours at 50-55° C. The suspension is then cooled to 20-25° C. and poured, under stirring, into 100 ml of cold (0-5° C.) water. The suspension is stirred for 30 minutes and the solid is filtered off, washed by water and dried at 40-50° C. Yield: 2.44 g (76.5percent).460 mg of the amide (7) from the was dissolved in 30 ml of dichloromethane. 560 mg of m-chloroperbenzoic acid (purity 70-75percent) was added. The reaction mixture was stirred overnight at reflux. The reaction was monitored with HPLC. The reaction mixture was washed successively with 2.x.20 ml of a sodium sulfite solution, 2.x.20 ml of saturated aqueous NaHCO3 and 20 ml of brine. The organic layer was dried (Na2SO4), filtrated and evaporated under reduced pressure yielding the epoxide (5A) as yellow solid material. Isolated yield: 400 mg (82percent). 1H- and 13C-NMR confirmed the expected structure. HPLC: 96percent purity(1)