Tributyltin Chloride → HCID 178439891, compound

Participants

Reaction Steps

A mixture of 4-methyl-2-propyl-1-[[2-(2-cyanophenyl)-5-pyridinyl]methyl]-1H-benzimidazol (0.87 g, 2.39 mmol), NaN3 (0.77 g, 11.94 mmol), and tri-n-butyltin chloride (3.88 g, 11.94 mmol) in xylenes (20 mL) was heated under reflux for 20 h. The reaction mixture was concentrated and 2N HCl was added. The mixture was extracted with ether (discarded) and adjusted to pH 5 with 50% NaOH. The aqueous phase was extracted with CH2Cl2, and the extracts were washed with water, dried, and concentrated. Purification by flash chromatography (5% MeOH/CH2Cl2) and recrystallization from EtOH/EtOAc/ether gave 0.45 g (45%) of product as a white solid, mp 169°-170° C.

Provenance & Evidence