Potassium Carbonate → 2-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate

Participants

Reaction Conditions

Reaction Steps

A heterogeneous mixture of 2-mercapto-5-nitropyridine (4) (46 mg, 0.29 mmol), 2-bromoethyl-3-chlorobenzoate (3) (77 mg, 0.29 mmol), and K2CO3 (0.160 g, 1.1 mmol) in acetone (1 mL) was stirred at 55° C. for 5 h. The cooled reaction mixture was filtered through Celite®, concentrated, and then purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)thio]ethyl-3-chlorobenzoate (5) as a white solid. 1H NMR (CDCl3): δ 9.22 (d, J=1.8 Hz, 1H), 8.24 (dd, J=2.4 and 9.0 Hz, 1H), 7.95-7.91 (m, 1H), 7.90 (t, J=0.9 Hz, 1H), 7.56-7.51 (m, 1H), 7.39 (d, J=8.1 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 4.61 (t, J=6.6 Hz, 2H), 3.68 (t, J=6.6 Hz, 2H)

Provenance & Evidence