Thiophenol → HCID 67336266, compound

Participants

Reaction Steps

Add sodium hydride (25 mg, 0.62 mmol, 60% dispersion in mineral oil) to benzenethiol (0.06 mL, 0.51 mmol) in anhydrous DMF (2 mL). Stir the mixture under nitrogen for 5 min and then add 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (198 mg, 0.51 mmol) in anhydrous DMF (2 mL) followed by catalytic potassium iodide (1 mg). Stir the reaction at 45° C. for 12 h then cool to room temperature and partition between EtOAc/water. Wash the organic phase with brine. Dry the organic phase over MgSO4, filter and concentrate in vacuo to give a yellow oil. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give 3-tert-butoxycarbonyl-7-chloro-6-phenylthiomethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (200 mg, 98%).

Provenance & Evidence