2-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate → 2-[(5-Nitro-2-pyridinyl)sulfinyl]ethyl-3-chlorobenzoate

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Reaction Steps

A solution of 2-(5-nitro-2-pyridinylthio)ethyl-3-chlorobenzoate, (5) [20 mg, 0.059 mmol; prepared according to the method outlined in Scheme 2; 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)] and m-chloroperbenzoate (m-CPBA) 50%, 21 mg, 0.060 mmol) was stirred at room temperature for 1.25 h. The reaction mixture was then diluted with dichloromethane and washed with saturated aqueous solution of NaHCO3 and then dried over anhydrous MgSO4. The crude product was purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)sulfinyl]ethyl-3-chlorobenzoate (6). LCMS: purity: 99%; MS (m/e): 355 (MH+).

Provenance & Evidence