Cesium carbonate → 4-[[2-(Diethylamino)ethyl]thio]benzenamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-aminothiophenol (23.0 mmol, 2.88 g) in DMF (23 mL) was added 2-(diethylamino)ethyl chloride hydrochloride (11.5 mmol, 1.98 g) and cesium carbonate (34.5 mmol, 11.2 g). The resulting mixture was heated to 60° C. for 3 hours. The solvent was removed by rotary evaporation. The residue was partitioned between dichloromethane and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography eluting with 5% methanol in dichloromethane with 1% triethylamine, giving the title compound (1.26 g, 49%). 1H NMR (CDCl3): δ 0.98 (6H, t, J=7.0 Hz), 2.51 (4H, q, J=7.1 Hz), 2.65 (2H, t, J=8.1 Hz), 2.85 (2H, t, J=8.3 Hz), 6.61 (2H, d, J=8.6 Hz), 7.25 (2H, d, J=8.6 Hz). LCMS m/z=225 (m+H+).

Provenance & Evidence