Benzyl Bromide → 1'-benzyl-2'-(benzylthio)-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one

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2-Bromo-2′-thioxo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazolidin]-5′-one (0.285 g, 0.9 mmol) was dissolved in THF (20 mL) and cooled to 0° C. in an ice bath. Sodium hydride (50% dispersion in oil, 26 mg, 1.08 mmol) was added and the mixture was stirred for 15 min. Benzyl bromide (0.13 ml, 1.08 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The mixture was cooled to 0° C. again and a further portion of sodium hydride (50% dispersion in oil, 26 mg, 1.08 mmol) was added. The mixture was stirred for 15 min, benzyl bromide (0.13 mL, 1.08 mmol) was added and the reaction mixture was stirred at room temperature for 18 hr. Solvent was evaporated under reduced pressure. The residue was dissolved in water and extracted with dichloromethane (×3). The organic extracts were combined, dried (MgSO4), and concentrated in vacuo. The crude residue purified on silica gel using ethyl acetate in iso-hexane (1:1) to afford the title compound as a colourless oil (0.25 g, 56%).

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