Potassium Hydroxide → Methyl 4-(1H-imidazole-2-carbonyl)benzoate

HRID 1059392Notes

Reaction equation

HRID 1059392 reaction equation
CN(C)S([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][CH2:21]C(C)(C)N=2)=[CH:15][CH:14]=1)[OH:12])(=O)=O.[OH-:27].[K+]>C(O)C>[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:20][CH3:21])=[O:27])=[CH:15][CH:14]=1)=[O:12].[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH:11]([OH:12])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:20][CH3:21])=[O:27])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18670283N,N-Dimethyl-2-[[4-(4,4-dimethyl-2-oxazolin-2-yl)phenyl]hydroxymethyl]imidazole-1-sulfonamide

Product 2

HCID 3446559Methyl 4-(1H-imidazole-2-carbonyl)benzoateHCID 18670386Methyl 4-[(imidazol-2-yl)hydroxymethyl]benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.70 g of N,N-dimethyl-2-[[4-(4,4-dimethyl-2-oxazolin-2-yl)phenyl]hydroxymethyl]imidazole-1-sulfonamide in ethanol was added 50 ml of a 2% aqueous solution of potassium hydroxide and the resulting mixture was heated under reflux for 15 hours. After distilling off the solvent under reduced pressure, 50 ml of methanol and 5 ml of conc. sulfuric acid were added to the residue and the resulting mixture was heated under reflux for 10 hours. After distilling off methanol under reduced pressure, the residue was distributed into ethyl acetate and an aqueous solution of sodium bicarbonate. The organic layer was extracted, washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.38 g of methyl 4-[(imidazol-2-yl)carbonyl]benzoate and 0.21 g of methyl 4-[(imidazol-2-yl)hydroxymethyl]benzoate each as a colorless oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 15 hours
  3. distillationAfter distilling off the solvent under reduced pressure, 50 ml of methanol and 5 ml of conc. sulfuric acid
  4. additionwere added to the residue
  5. temperaturethe resulting mixture was heated
  6. temperatureunder reflux for 10 hours
  7. distillationAfter distilling off methanol under reduced pressure
  8. extractionThe organic layer was extracted
  9. washwashed successively with water
  10. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  11. distillationAfter distilling off the solvent under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-412e7b109bab4b498c4e70a3ad06b9e5
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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