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

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Reaction Steps

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.

Provenance & Evidence