Benzyl Bromide → HCID 501233, compound

HRID 1829733Notes

Reaction equation

HRID 1829733 reaction equation
[SH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(=O)CC>[C:16]1([CH2:15][S:1][C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178516238HCID 178516238, compound

Product 1

HCID 501233HCID 501233, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a mixture of 10.0 g of 2-mercapto-3-pyridinol, 11.0 g of potassium carbonate and 100 mL of 2-butanone was added dropwise with stirring, 13.3 g of benzyl bromide. After stirring at 22° C. for two hours, the mixture was heated to reflux for thirty minutes. The reaction mixture was concentrated under reduced pressure, the residue treated with water, and the mixture brought to pH 6 by the addition of acetic acid. The crude product was filtered and recrystallized from toluene to give 11.1 g of the title compound as a grey crystalline solid, mp 103–104° C. The structure of the product was confirmed by its 1H nmr and mass spectra.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring at 22° C. for two hours
  3. temperaturethe mixture was heated
  4. temperatureto reflux for thirty minutes
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionthe residue treated with water
  7. additionthe mixture brought to pH 6 by the addition of acetic acid
  8. filtrationThe crude product was filtered
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-997956b4e4d94a9bb1e879853d7bf065
Source dataset
uspto-grants-2006_06
Patent number
US07064139B2

Reaction notes

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