Water → HCID 67335857, compound

Participants

Reaction Steps

Dissolve benzylmercaptan (230 mg, 1.84 mmol) in anhydrous DMF (5 mL). Add sodium hydride (100 mg, 2.5 mmol, 60% dispersion in mineral oil) and stir the mixture for 10 min. Add then a solution of 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (550 mg, 1.67 mmol) in anhydrous DMF (1 mL). Stir under nitrogen at room temperature overnight. Pour reaction mixture into water (150 mL) and extract with DCM (3×50 mL). Wash the combined organic extracts with brine, dry over Na2SO4, filter and concentrate in vacuo to afford crude 6-benzylthiomethyl-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (1.13 g) suitable for use without additional purification.

Provenance & Evidence