Thionyl Chloride → HCID 15166211, compound

HRID 609828Notes

Reaction equation

HRID 609828 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][N+:12]([O-:15])=[C:11]([CH3:16])[C:10]=1[CH3:17].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:3][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][N+:12]([O-:15])=[C:11]([CH3:16])[C:10]=1[CH3:17]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 15166210HCID 15166210, compound

Product 1

HCID 15166211HCID 15166211, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.0 ml of thionyl chloride was gradually added to a solution of 0.92 g (5 mmol) of 4-(2-hydroxyethoxy)-2,3-dimethylpyridine N-oxide in 10 ml of chloroform under cooling with ice. The obtained mixture was heated under reflux for 2 hours, cooled by allowing to stand, neutralized with a saturated aqueous solution of sodium hydrogencarbonate and extracted with 100 ml of methyl ethyl ketone twice. The extract was dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography (solvnet: chloroform/methanol=19:1) to obtain 0.56 g of 4-(2-chloroethoxy)-2,3-dimethylpyridine N-oxide as a colorless crystal.

Workup

  1. temperatureunder cooling with ice
  2. temperatureThe obtained mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled
  5. extractionextracted with 100 ml of methyl ethyl ketone twice
  6. dry with materialThe extract was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. custompurified by silica gel column chromatography (solvnet: chloroform/methanol=19:1)

Sources & evidence

ORD record
ord-05e976e7f6a745948e84103c821a1c06
Source dataset
uspto-grants-1999_12
Patent number
US05998445

Reaction notes

Loading…