Toluene → 3-[(3,4-dichlorophenyl)methyl]-2-(1-methylethyl)-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium bromide (419 mg) was added to a stirred mixture of Intermediate 2 (500 mg, 2.60 mmol) and 3,4-dichlorobenzylbromide (624 mg) in sodium hydroxide 20% aq (3.50 mL) and Toluene (9 mL). The RM was stirred at 30° C. under nitrogen atm for 3 hours. An excess of sat NH4Cl aq solution was added and the mixture was extracted with EtOAc (3×30 ml). The organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (630 mg). LC/MS MH+ 351/353, Rt 3.16 min (5 minute run).

Provenance & Evidence