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

HRID 72662Notes

Reaction equation

HRID 72662 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:12][S:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:7][C:8]=1[N+:9]([O-:11])=[O:10].[OH:19]O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:12][S:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:19])=[N:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 67994824Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate

Product 1

HCID 70652453Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylsulfinyl)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-d153efe04f8a43ccaf3b173730dc75ce
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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