Sodium Iodide → HCID 67336269, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (42.3 g, 128 mmol) in acetone (400 mL). Warm to 50° C., and then add potassium carbonate (26.5 g, 192 mmol) and sodium iodide (1.92 g, 12.8 mmol). With stirring, add 2-mercaptoimidazole (13.46 g, 134.4 mmol). Allow the mixture to stir at room temperature for 16 h. Filter the solid from this mixture, and wash the solid with acetone. Concentrate the filtrate in vacuo to a pink solid. Add DCM (400 mL) and 3% aqueous NaHCO3 (400 mL). Collect the organic layer, and back extract the aqueous with DCM (2×100 mL). Combine the organic extracts and wash successively with brine (2×100 mL) and saturated aqueous NaHCO3 (1×50 mL). Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain 3-tert-butoxycarbonyl-7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an off-white solid (46.3 g, 92%). MS (ES+) m/z: 394.3 (M+H)+.

Provenance & Evidence