Potassium Hydroxide → Pyridine, 2-(1H-imidazol-2-ylmethyl)-

HRID 1059390Notes

Reaction equation

HRID 1059390 reaction equation
CN(C)S([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)(=O)=O.[OH-].[K+]>C(O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][C:7]1[NH:8][CH:9]=[CH:10][N:6]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18670131HCID 18670131, compound

Product 1

HCID 18670424Pyridine, 2-(1H-imidazol-2-ylmethyl)-Yield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.21 g of N,N-dimethyl[2-(pyridin-2-ylmethyl)imidazol-1-yl]sulfonamide in ethanol (2 ml) was added a 2% aqueous solution (20 ml) of potassium hydroxide and the resulting mixture was heated under reflux for 11 hours. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.053 g of the title compound as a colorless oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 11 hours
  3. distillationAfter distilling off the solvent under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-ef9312a1c2ec499bbd6e8cedad8f66e4
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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