Chemical Properties
White to light yellow crystal powde
Uses
3-(Trifluoromethyl)benzamide can be prepared from 1-bromo-3-trifluoromethylbenzene via palladium-catalyzed aminocarbonylation with formamide.
It forms the core moiety of
N-[(substituted 1
H-imidazol-1-yl)propyl]benzamides, with potential as antihypertensive agents.
General Description
3-(Trifluoromethyl)benzamide can be prepared from 1-bromo-3-trifluoromethylbenzene via palladium-catalyzed aminocarbonylation with formamide. It forms the core moiety of
N-[(substituted 1
H-imidazol-1-yl)propyl]benzamides, with potential as antihypertensive agents.
Synthesis
GENERAL STEPS: To a flame-dried, resealable 2-5 mL Pyrex reaction vessel were added the solid reactants: m-trifluoromethylbenzonitrile (1.0 mmol) and Cs2CO3 (1.5 mmol). The reaction vessel was sealed with a rubber septum and pyrrolidone (2 mL/mmol [0.5 M]) was injected through the septum. Subsequently, the rubber septum was replaced with a PTFE screw cap. The sealed reaction vessel was heated in an oil bath at 130°C for 2 hours. Upon completion of the reaction, the resulting suspension was cooled to room temperature, filtered through a diatomaceous earth pad and eluted with a solvent mixture of CH2Cl2/MeOH (7:3) to remove inorganic salts. Finally, the filtrate was concentrated and the residue was purified by silica gel column chromatography to afford the target product 3-(trifluoromethyl)benzamide.
References
[1] Tetrahedron Letters, 2012, vol. 53, # 23, p. 2860 - 2863
[2] Catalysis Science and Technology, 2015, vol. 5, # 5, p. 2865 - 2868
