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

Participants

Reaction Conditions

Reaction Steps

1′-Benzyl-2′-(benzylthio)-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one (0.25 g, 0.5 mmol) and ammonium iodide (0.43 g, 3 mmol) were suspended in 7 N NH3/methanol solution (10 mL). The mixture was heated at 90° C. for 18 hr. The solution was concentrated in vacuo and the crude residue partitioned between water and dichloromethane. The product was extracted into dichloromethane (×3), the organic extracts were combined, dried (MgSO4) and concentrated in vacuo. The crude residue was purified on silica gel using 7 N NH3/methanol in dichloromethane (1:9) to afford the title compound as a foam (80 mg, 41%).

Provenance & Evidence