4-Aminothiophenol → HCID 21543863, compound

Participants

Reaction Steps

A stirred slurry of ethyl 2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-3-carboxylate (79c) (5.14 g, 16.6 mmol), 4-aminothiophenol (4.49 g, 35.9 mmol) and LiBr (8.66 g, 99.7 mmol) in 50 mL N,N′-dimethylformamide was heated to 160° C. for 24 h. The cooled mixture was diluted with 200 mL 1N HCl and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with 1N HCl, 20% K2CO3, and brine. The organic solution was dried (MgSO4), filtered, and evaporated. The crude product was triturated (EtOH/EtOAc) to give a white powder (2.96 g, 75%). 1H NMR (300 MHz, CDCl3) δ 2.55-2.72 (m, 2H), 2.90 (dd, J=7 Hz, J=14 Hz, 1H), 3.19 (dd, J=7 Hz, J=14 Hz, 1H), 3.70 (quin, J=7 Hz, 1H), 7.03 (d, J=7 Hz, 1H), 7.10-7.40 (m, 8H), 7.71 (br s, 1H). MS APCI, m/z=238 (M+1). LC/MS: 2.24 min.

Provenance & Evidence