Sodium Sulfite → HCID 23110952, compound

HRID 2373683Notes

Reaction equation

HRID 2373683 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([S:15][CH3:16])[CH:9]=[C:8]([CH3:17])[N:7]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([S:15]([CH3:16])=[O:26])[CH:9]=[C:8]([CH3:17])[N:7]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 23110953HCID 23110953, compound

Product 1

HCID 23110952HCID 23110952, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(2-methoxyethyl)oxy]-6-methyl-4-methylthio-3-nitropyridine (2.00 g, 7.74 mmol) was dissolved in dichloromethane (25 mL). m-Chloroperbenzoic acid (60%, 5.0 g, 17.38 mmol) was added to the solution, followed by stirring at room temperature for 12 hours. Saturated aqueous sodium sulfite was added to the reaction mixture, followed by stirring for 1.5 hours so that excessive m-chloroperbenzoic acid was deactivated. The organic layer was washed with saturated brine, followed by drying over sodium sulfate anhydrate and concentration under reduced pressure. The obtained residue was recrystallized from ether, to thereby yield 2-[(2-methoxyethyl)oxy]-6-methyl-4-methylsulfinyl-3-nitropyridine as colorless crystals (1.93 g, 91%).

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialby drying over sodium sulfate anhydrate and concentration under reduced pressure
  3. customThe obtained residue was recrystallized from ether

Sources & evidence

ORD record
ord-877227eca39a403389fdf3d63fd2db3c
Source dataset
uspto-grants-2008_12
Patent number
US07459552B2

Reaction notes

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