Diphenylmethylidenehydrazine → (E)-N-[(E)-(3-bromothiophen-2-yl)methylideneamino]-1,1-diphenylmethanimine

Participants

Reaction Conditions

Reaction Steps

3-Bromothiophene-2-carbaldehyde (8.0 g, 41.9 mmol) and (diphenylmethylene)hydrazine (9.45 g, 48.2 mmol) were dissolved in ethanol (60 mL) and the solution was heated at 80° C. overnight. Volatiles from the reaction mixture were removed via rotary evaporation and the crude product was purified by normal phase silica gel chromatography (ISCO-Combiflash) eluting with a gradient of 0-30% hexane and EtOAc. The pure fractions were combined and evaporated to give the title compound as a mixture of cis/trans isomers (15.0 g, 97%). ESI-MS m/z [M+H]+ calc'd for C18H13BrN2S, 370. found, 370.

Provenance & Evidence