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

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium hydroxide 30% in water (12.06 g) and toluene (20 mL), tropolone tosylate (2.5 g), tert-butylcarbamidine hydrochloride (1.236 g) and tetrabutylammonium bromide (1.167 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 (3×50 ml). The combined organics were 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%-95% gross gradient). The desired fractions were combined and concentrated under vacuum to yield the title compound (1.9 g). LC/MS MH+ 203, Rt 0.62 min (2 minute run).

Provenance & Evidence