Dimethyl Sulfoxide → 2-(methylsulfonyl)-5-nitropyridine

HRID 1860595Notes

Reaction equation

HRID 1860595 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6]C(SC)=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:12][S:13]([O-:15])=[O:14].[Na+].O.[CH3:18]S(C)=O>>[N+:1]([C:4]1[CH:5]=[N:6][C:12]([S:13]([CH3:18])(=[O:15])=[O:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 2733271Sodium methanesulfinateHCID 44393132-(Methylthio)-5-nitropyridine

Product 1

HCID 12115522-(methylsulfonyl)-5-nitropyridine

Conditions

Temperature
100 °C

Procedure

Alternatively, 3-nitro-6-(methylsulfonyl)pyridine was prepared by dissolving of 3-nitro-6-(methylthio)pyridine (1 equivalent) and sodium methane sulfinate in DMSO and heating at 100° C. for 2 hours. The reaction was diluted with a large excess of water and extracted with ethyl acetate. The organic layer was concentrated in vacuo to give the desired 3-nitro-6-(methylsulfonyl)pyridine.

Workup

  1. customAlternatively, 3-nitro-6-(methylsulfonyl)pyridine was prepared
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-5b9db740404c425fa5e386faaffa45a8
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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