3-Bromo-N-cyclopropyl-5-[(1E)-3-methoxyprop-1-en-1-yl]-4-methylbenzamide → 3-bromo-N-cyclopropyl-5-(3-methoxypropyl)-4-methylbenzamide

Participants

Reaction Steps

To a solution of 3-bromo-N-cyclopropyl-5-[(1E)-3-methoxyprop-1-en-1-yl]-4-methylbenzamide (1 eq.) from the previous step in refluxing toluene (0.1 M) was added portionwise benzenesulfonyl hydrazide (6 eq.) over 2 h. After heating at reflux for another hour, the now black reaction suspension was cooled to RT, quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a yellow oil.

Provenance & Evidence