Thionyl Chloride → 2-Chloro-4-(chloromethyl)-6-methylpyridine

HRID 2099825Notes

Reaction equation

HRID 2099825 reaction equation
[Cl: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: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 22504306(2-Chloro-6-methylpyridin-4-yl)methanol

Product 1

HCID 216981672-Chloro-4-(chloromethyl)-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Chloro-6-methylpyridin-4-yl)methanol (0.212 g, 1.35 mmol) and thionyl chloride (0.12 mL, 1.62 mmol) were combined in methylene chloride (4 mL) and stirred at room temperature for 4 h. The solvents were removed and the product dried under vacuum for several hours to afford 0.24 g (quant.) as a clear oil which was used without purification. Mass spec.: 176.0 (MH)+.

Workup

  1. customThe solvents were removed
  2. customthe product dried under vacuum for several hours
  3. customto afford 0.24 g (quant.) as a clear oil which
  4. customwas used without purification

Sources & evidence

ORD record
ord-2f6899c5c0574523b8288fa8836090b8
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

Loading…