Ethanol → 2-(Benzylthio)-3-nitropyridine

Participants

Reaction Conditions

Reaction Steps

Ethanol (150 mL) was added to a mixture of 2-chloro-3-nitro-pyridine (5 g, 31.54 mmol) and potassium carbonate (4.8 g, 34.7 mmol). Benzyl mercaptan (4.09 mL, 34.7 mmol) was added followed by water (30 mL). The mixture stirred at 25° C. for 4 h. Water (350 mL) was added and the product precipitated. The solid was collected by vacuum filtration, rinsed with water (100 mL) and dried in vacuo for 4 h to afford the desired product, 2-benzylsulfanyl-3-nitro-pyridine (6.6 g, 26.8 mmol, 85%), as a yellow powder. 1H NMR (400 MHz, DMSO-d6) δ: 4.47 (2H, s), 7.21-7.31 (3H, m), 7.40-7.45 (3H, m), 8.58 (1H, dd, J1=8.6 Hz, J2=1.7 Hz), 8.83 (1H, dd, J1=4.7 Hz, J2=1.7 Hz).

Provenance & Evidence