Iodine → 2-(4-(methylthio)phenyl)-4,5-dihydro-1H-imidazole

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Reaction Steps

To a solution of 4-(methylthio)benzaldehyde (1-Im-1, 10 g, 1.0 eq) in 1000 mL of t-BuOH, ethylene diamine (1.1 eq) was added. The mixture was stirred at rt under Ar for 30 min, then K2CO3 (3.0 eq) and I2 (1.25 eq) were added to the mixture. This mixture was stirred at 70° C. for 3 h, then was quenched with aqueous Na2SO3 until the color of iodine disappeared, then extracted with CHCl3. The organic layer was washed with NaHCO3 and brine and dried with Na2SO4. The solvent was removed to give 2-(4-(methylthio)phenyl)-4,5-dihydro-1H-imidazole (compound 2-Im-1).

Provenance & Evidence