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

HRID 1734259Notes

Reaction equation

HRID 1734259 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-806df38f5dff4234bc866657aa873340
Source dataset
uspto-grants-1996_07
Patent number
US05532354

Reaction notes

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