2-Methoxyethanol → HCID 23110953, compound

HRID 2373682Notes

Reaction equation

HRID 2373682 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([S:11][CH3:12])[CH:5]=[C:4]([CH3:13])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][CH2:22][CH2:23][OH:24]>>[CH3:20][O:21][CH2:22][CH2:23][O:24][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([S:11][CH3:12])[CH:5]=[C:4]([CH3:13])[N:3]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 11430Potassium CarbonateHCID 10560803HCID 10560803, compound

Product 1

HCID 23110953HCID 23110953, compound

Conditions

Temperature
60 °C

Procedure

2-Chloro-6-methyl-4-methylthio-3-nitropyridine (2.80 g, 12.81 mmol) was dissolved in 2-methoxyethanol (40 mL). Potassium carbonate (1.90 g, 13.75 mmol) was added to the solution, followed by stirring for 5 hours at 60° C. The mixture was allowed to stand for cooling. Subsequently, the resultant mixture was extracted with ether-water, and the organic layer was washed with saturated brine, followed by drying sodium sulfate anhydrate and concentration under reduced pressure. The obtained residue was purified through silica gel column chromatography [(1) (eluent: n-hexane/ethyl acetate=4/1→n-hexane/ethyl acetate=2/1), (2) (eluent: chloroform)], to thereby yield 2-[(2-methoxyethyl)oxy]-6-methyl-4-methylthio-3-nitropyridine as a pale yellow oil (2.21 g, 67%).

Workup

  1. temperaturefor cooling
  2. extractionSubsequently, the resultant mixture was extracted with ether-water
  3. washthe organic layer was washed with saturated brine
  4. customby drying
  5. concentrationsodium sulfate anhydrate and concentration under reduced pressure
  6. customThe obtained residue was purified through silica gel column chromatography [(1) (eluent: n-hexane/ethyl acetate=4/1→n-hexane/ethyl acetate=2/1), (2) (eluent: chloroform)]

Sources & evidence

ORD record
ord-4d1245a9fda84a209dc70b8df5effdb4
Source dataset
uspto-grants-2008_12
Patent number
US07459552B2

Reaction notes

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