Thionyl Chloride → 2-Chloro-3-(chloromethyl)-5-methylpyridine

HRID 413475Notes

Reaction equation

HRID 413475 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:11]([CH2:12]O)=[CH:10][C:9]([CH3:14])=[CH:8][N:7]=1>C(Cl)Cl>[Cl:5][C:6]1[C:11]([CH2:12][Cl:3])=[CH:10][C:9]([CH3:14])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12056721(2-Chloro-5-methylpyridin-3-yl)methanol

Product 1

HCID 112060822-Chloro-3-(chloromethyl)-5-methylpyridineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2.73 g, 0.023 moles) was added slowly to a well-stirred solution of 2-chloro-3-hydroxymethyl-5-methylpyridine (1.2 g, 0.0076 moles) in methylenechloride (20 ml) at 0° C. temperature over a period of 20 minutes. The reaction mass was further stirred for 6 hours at the same temperature. The solvent and excess thionylchloride was removed under reduced pressure and the mass was quenched with water (25 ml). The mass was extracted with methylene chloride (2×50 ml) and the layers separated. The organic layer was dried over sodium sulphate and the solvent removed under reduced pressure. The residue so obtained was subjected to chromatographic purification on silica gel to give 2-chloro-3-chloromethyl-5-methylpyridine as a solid in 92% yield.

Workup

  1. customThe solvent and excess thionylchloride was removed under reduced pressure
  2. customthe mass was quenched with water (25 ml)
  3. extractionThe mass was extracted with methylene chloride (2×50 ml)
  4. customthe layers separated
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. customthe solvent removed under reduced pressure
  7. customThe residue so obtained
  8. customwas subjected to chromatographic purification on silica gel

Sources & evidence

ORD record
ord-e1a03e75e8ac41189eb6b7d05587aeb5
Source dataset
uspto-grants-2003_05
Patent number
US06566528B1

Reaction notes

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