Sodium Hydroxide → 2-(1-methylethyl)cyclohepta[d]imidazol-4(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium hydroxide 30% in water (24 g) and toluene (30 mL), tropolone tosylate (5 g), isopropylcarbamidine hydrochloride (2.2 g) and tetrabutylammonium bromide (2.3 g) were added successively and the RM was stirred and heated at 30° C. for 1 hour. The reaction mixture was cooled down to room temp, diluted with an excess of sat. aq. NH4Cl solution and then extracted with EtOAc (3×40 ml). The aqueous phase was again extracted with EtOAc (3×50 ml). All the organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified by reverse phase chromatography using an acetonitrile-0.1% TFA:Water-0.1% TFA 5%-50% gradient and a 50%-95% gradient. The desired fractions were combined and concentrated under vacuum to yield the title compound (3.4 g). LC/MS MH+ 189, Rt 1.18 min (5 minute run)

Provenance & Evidence