Thionyl Chloride → 4-(Chloromethyl)-2,6-dimethylpyridine

HRID 1682204Notes

Reaction equation

HRID 1682204 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([CH3:10])[N:3]=1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][Cl:13])[CH:5]=[C:4]([CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 38250772,6-Dimethyl-4-(hydroxymethyl)pyridine

Product 1

HCID 135828144-(Chloromethyl)-2,6-dimethylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 77 ml of CHCl3 was dissolved 7.00 g (0.0511 mole) of (2,6-dimethyl-4-pyridyl)methanol and with stirring at room temperature, 15.3 ml of thionyl chloride was added dropwise. After completion of the dropwise addition, the mixture was stirred for 3 hours and concentrated. The residue was diluted with aqueous sodium hydrogen carbonate solution and extracted with AcOEt (100 ml×3). The extract was dried over MgSO4 and distilled to remove AcOEt. The procedure gave 6.37 g of (2,6-dimethyl-4-pyridyl)methyl chloride as oil.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe mixture was stirred for 3 hours
  3. concentrationconcentrated
  4. additionThe residue was diluted with aqueous sodium hydrogen carbonate solution
  5. extractionextracted with AcOEt (100 ml×3)
  6. dry with materialThe extract was dried over MgSO4
  7. distillationdistilled
  8. customto remove AcOEt

Sources & evidence

ORD record
ord-cdc0f2df8c8f43f3aa3313c6c3a1f9a7
Source dataset
uspto-grants-1992_12
Patent number
US05175301

Reaction notes

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