Thionyl Chloride → 2-Chloromethyl-5-benzyloxy-4-pyridone

HRID 5518Notes

Reaction equation

HRID 5518 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH2:11][C:12]([CH2:15]O)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH2:11][C:12]([CH2:15][Cl:20])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 665918345-Benzyloxy-2-hydroxymethyl-4-pyridone

Product 1

HCID 677480612-Chloromethyl-5-benzyloxy-4-pyridone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 5-benzyloxy-2-hydroxymethyl-4-pyridone (33 g) in benzene (500 ml) was added thionyl chloride (28.4 ml) at ambient temperature under stirring. After being stirred at the same temperature for 30 minutes, the mixture was refluxed for 4 hours. The resulting mixture was cooled to ambient temperature. The precipitate was collected by filtration, washed with benzene and dried under reduced pressure to give 5-benzyloxy-2-chloromethyl-4-pyridone (41.5 g).

Workup

  1. stirringAfter being stirred at the same temperature for 30 minutes
  2. temperaturethe mixture was refluxed for 4 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with benzene
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c5330d0eb2d04a46bc2e78047215f6c4
Source dataset
uspto-grants-1993_09
Patent number
US05244890

Reaction notes

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