Reaction #159844

Reaction equation

Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate

hydrogen peroxide

→

titled compound

Yield 95.0%

Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylsulfinyl)acetate

Yield 95.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   Otherthe solvent was evaporated in vacuo
2. 2
   OtherThe mixture was purified by column chromatography

Procedure

Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate (1.0 mmol, 0.27 g) and hydrogen peroxide 30% (1.0 mmol, 0.12 mL) were dissolved in acetic acid (10 mL). The mixture stirred at r.t. for 6 hrs and the solvent was evaporated in vacuo. The mixture was purified by column chromatography using 1:1 PE/EtOAc to give the titled compound. Yield 95%; 1H-NMR (DMSO-D6) δ: 3.74 (s, 3H, OCH3), 3.76 (d, 1H, J=14.2 Hz), 4.02 (d, 1H, J=14.2 Hz,), 4.07 (s, 3H, OCH3), 4.27 (d, 1H J=12.9 Hz, CH), 4.42 (d, 1H J=12.9 Hz, CH), 7.76 (d, 1H, J=8.6 Hz, Py-H), 7.94 (d, 1H, J=8.6 Hz, Py-H); 13C-NMR (DMSO-D6) δ: 51.90, 55.1756.52, 57.31, 124.13, 130.82, 141.18, 146.90, 166.11, 205.26. HR-MS (ESI+) m/z 289.0428 [M+H]+ C10H12N2O6S, requires 288.0416.

Source