4-(Trifluoromethyl)benzamide

White to light yellow crystal powde

Synthesis of compound C; Aqueous ammonia (2 ml) was added to 4-(trifluoromethyl)-benzoyl chloride (417 mg, 2 mmol) at room temperature with stirring, and the reaction was allowed to proceed for 3 hours. The completion of the reaction was confirmed using a TLC plate (ethyl acetate:hexane = 1:2), and the reaction product was introduced into 10 ml of water, followed by extraction with ethyl acetate (10 ml .x. 3). The ethyl acetate layer was washed with water (10 ml .x. 2) and with saturated saline (10 ml), dried over magnesium sulfate, and then filtered to obtain a crude product via removal of a solvent by distillation under reduced pressure (355 mg, 2.0 mmol). The resultant was recrystallized with a mixed solvent of ethyl acetate/hexane to obtain compound C (white, needle-like crystal, 359 mg). Yield: 95percent; m.p.: 186.5-187.5°C General procedure: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde(7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added, the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed, and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH.General procedure: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde (7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added, the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed, and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH.General procedure: To an oven dried Schlenk carousel tube containing the appropriate nitrile (1 mmol) was added palladium acetate (11 mg, 5 molpercent), 2, 2'-bipyridine (7.8 mg, 5 molpercent) and water (2 mL, 0.5 M). The tube was then sealed and the reaction mixture heated at 70 °C for 24 hours. After being allowed to cool to room temperature, the reaction mixture was diluted with methanol (5 mL) and the solvent removed in vacuo on a rotary evaporator whilst azeotroping with toluene. Where the reaction had gone to quantitative conversion or the starting nitrile was volatile, the crude reaction mixture was passed through a short plug of silica to remove the catalyst (eluting with DCM/MeOH, 95:5). Otherwise, the primary amide products were purified by column chromatography (eluting with DCM/MeOH, 95:5, unless otherwise stated).General procedure: In a Schlenk-tube of approximately 12 mL volume, 0.05 mmol Ru(II)-precursor (1, 2 or RuClA solution of 4- (trifluoromethyl) benzonitrile (171 mg, 1 mmol), [Cp * Rh (HGeneral procedure: To a stirred solution of half-sandwich ruthenium complex (0.25molpercent) in 2.0mL of isopropanol were added NaOH (0.3mmol) and benzonitrile (0.3mmol) followed by stirring for 4h at 353K. After completion of the reaction (monitored by TLC), the resulting solution was evaporated to dryness at reduced pressure. The crude products loaded directly onto a column of silica gel and purified by column chromatography to yield the corresponding amides [15].In the reaction vessel was added 25molpercent Cu, the reaction tube was evacuated, filled with oxygen, 0.2 mmol of 4-trifluoromethylbenzonitrile, 0.5 mmol of ammonium chloride and 2 ml of N, N-dimethylformamide were added in an atmosphere of oxygen, the reaction vessel was sealed, and reacted at 120 ° C, After the reaction was completed, it was washed with water, extracted with chloroform, dried and evaporated under reduced pressure to remove the solvent. The crude product was separated by column chromatography to give the desired product in a yield of 33percent.To a cold solution of 4-(trifluoromethyl)benzonitrile (0.500 g, 2.92 mmol) in DMSO (6.0 mL) was added HGeneral procedure: To a stirred solution of aryl halide (Br/I) (1 mmol) in dry dioxane in a 25 mL sealed tube, was added Pd(OAc)2 (5 molpercent), dppf (6 mol percent), DIPEA (2 mmol), imidazole (0.25 mmol), ammonium chloride (2 mmol) and then Co2(CO)8 (0.3 mmol). The seal tube was closed immediately and stirred at 90 °C for 3h. After the reaction time the reaction mixture was cooled to room temperature. The reaction mixture was filtered through celite pad and washed with dioxane, the filtrate was concentrated under reduced pressure and the residue obtained was purified by column chromatography.To β-ketodithioester 1 (1.0 mmol), 10 mL of 25percent aq. ammonia solution was added and the reaction mixture was refluxed at 100 °C with constant stirring for the stipulated period of time. After completion of the reaction (monitored by TLC), water (20 mL) was added to the reaction mixture followed by extraction with ethyl acetate (2 × 10 mL). The combined organic layer was dried over anhydrous NaGeneral procedure: To a stirred solution of aryl halide (Br/I) (1 mmol) in dry dioxane in a 25 mL sealed tube, was added Pd(OAc)2 (5 molpercent), dppf (6 mol percent), DIPEA (2 mmol), imidazole (0.25 mmol), ammonium chloride (2 mmol) and then Co2(CO)8 (0.3 mmol). The seal tube was closed immediately and stirred at 90 °C for 3h. After the reaction time the reaction mixture was cooled to room temperature. The reaction mixture was filtered through celite pad and washed with dioxane, the filtrate was concentrated under reduced pressure and the residue obtained was purified by column chromatography.General procedure for the synthesis of nitriles: A pressure tube was charged with an appropriate amount of Zn(OTf)To a solution of propionamidine hydrochloride (1.90 g, 17.5 mmol) and α, α, α-trifluoro-p-tolunitrile (2.0 g, 11.7 mmoles) in 30 mL of dimethylsulfoxide was added cesium carbonate (11.4 g, 34.9 mmol) and copper(I) bromide (0.3 g, 1.05 mmol) and the mixture was stirred and heated at 120 °C for 16 h, open to the air. After the reaction was completed, the reaction mixture was cooled and diluted with water, quenched with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The aqueous layer was separated and extracted twice with ethyl acetate. The combined ethyl acetate layers were washed with saturated EDTA aqueous solution and brine, dried over MgS0

Molecular Weight:189.13
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:189.04014830
Monoisotopic Mass:189.04014830
Topological Polar Surface Area:43.1
Heavy Atom Count:13
Complexity:194
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes