Cesium carbonate → N-benzhydrylidene-N'-[2-(benzhydrylidene-hydrazonomethyl)-thiophen-3-yl]-hydrazine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-benzhydrylidene-N′-[1-(3-bromo-thiophen-2-yl)-meth-(E)-ylidene]-hydrazine (10.8 g, 29.2 mmol) in toluene (200 mL) was added (diphenylmethylene)hydrazine (6.9 g, 35.1 mmol), cesium carbonate (16.2 g, 49.7 mmol), Pd(OAc)2 (1.31 g, 5.85 mol), and 1,1′-bis(diphenylphosphino)ferrocene (2.43 g, 4.4 mmol). The reaction mixture was heated at 100° C. for 8.5 h then cooled to room temperature, diluted with EtOAc and filtered over Celite, rinsing with EtOAc. The filtrate was concentrated and the residue was purified by silica gel chromatography with 10% to 20% EtOAc/heptane to give 12.8 g of N-benzhydrylidene-N′-[2-(benzhydrylidene-hydrazonomethyl)-thiophen-3-yl]-hydrazine as a viscous brown oil.

Provenance & Evidence