4-Chlorobutyrophenone → HCID 54553651, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chlorobutyrophenone (8.5 mL, 53 mmol) and 4-(2-(2-pyridyl)ethyl)-3-thiosemicarbazide (9.5 g, 48 mmol) in 400 mL of ethanol was heated under a nitrogen atmosphere to 75° C. and then at that temperature for 24 hours (overnight). The solvent was removed under reduced pressure to give 20.3 g of a yellow oil. This oil was triturated with EtOAc to separate the desired product from the thiosemicarbazide. The ethyl acetate was removed under reduced pressure and the residue chromatographed on 1 kg of silica gel (230-400 mesh) using 10-20% EtOAc-hexane as the eluent. The material collected (2.86 g, yellow solid) was recrystallized from isopropyl alcohol to give 2.30 g (13%) of the title compound as an off-white solid, mp 126-129° C.

Provenance & Evidence