4-Benzyloxybenzoylchloride → HCID 14049660, compound

HRID 466154Notes

Reaction equation

HRID 466154 reaction equation
[Cl:1][C:2]1[C:3]([OH:9])=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:10]([O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:9][C:3]2[C:2]([Cl:1])=[CH:7][NH:6][C:5](=[O:8])[CH:4]=2)=[O:23])=[CH:25][CH:26]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 37664104-BenzyloxybenzoylchlorideHCID 54679224Gimeracil

Product 1

HCID 14049660HCID 14049660, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 3.00 g quantity of 5-chloro-4-hydroxy-2-pyridone was suspended in 100 ml of pyridine. To the suspension was added 5.59 g of 4-benzyloxybenzoyl chloride with stirring at room temperature. The reaction mixture was stirred at 90° C. for 1.5 hours. The solvent was distilled off and ethyl acetate was added to the residue. The mixture was stirred at room temperature overnight. The ethyl acetate layer was concentrated and the residue was subjected to silica gel column chromatography using as an eluent 2% methanol-chloroform, giving 770 mg of the title compound in a yield of 10.5%.

Workup

  1. stirringThe reaction mixture was stirred at 90° C. for 1.5 hours
  2. distillationThe solvent was distilled off
  3. additionethyl acetate was added to the residue
  4. stirringThe mixture was stirred at room temperature overnight
  5. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-9141d0bb5383460090d2f0108b031475
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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