Benzoyl chloride → HCID 14049599, compound

HRID 466133Notes

Reaction equation

HRID 466133 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[C:12]([OH:18])=[CH:13][C:14](=[O:17])[NH:15][CH:16]=1>N1C=CC=CC=1>[Cl:10][C:11]1[C:12]([O:18][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][C:14]([O:17][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 54679224Gimeracil

Product 1

HCID 14049599HCID 14049599, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 1.76 ml quantity of benzoyl chloride was added to a suspension of 1.00 g of 5-chloro-4-hydroxy-2-pyridone in 30 ml of pyridine, and the mixture was stirred at room temperature for two hours. The solvent was distilled off and the residue was dissolved in a mixture solution of 60 ml of ethyl acetate and 30 ml of water. The ethyl acetate layer was separated, washed twice with 30 ml of water, dried on anhydrous sodium sulfate and concentrated. The concentrate was further washed with a small amount of ethanol, giving 2.11 g of the title compound in a yield of 86.8%.

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in a mixture solution of 60 ml of ethyl acetate and 30 ml of water
  3. customThe ethyl acetate layer was separated
  4. washwashed twice with 30 ml of water
  5. dry with materialdried on anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washThe concentrate was further washed with a small amount of ethanol

Sources & evidence

ORD record
ord-e3848625c1f748599a0d5cfde6487d66
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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