Ethyl Acetate → 7-chloro-3-(2-chlorobenzyl)-5-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

7-Chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-5-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.4 g, 0.68 mmol) was dissolved in 10% anisole in 1,1-dichloroethene (DCE, 3 mL) under nitrogen and AlCl3 (0.455 g, 3.42 mmol) was added in one portion. The resulting orange solution was heated to 85° C. for 1.5 h. The solution was allowed to cool. Ethyl acetate was added followed by ice water. This mixture was stirred for 30 min (turned from yellow to colorless) then partitioned and the organic layer was washed with water then brine. The organic layer was dried over MgSO4, then filtered to give a clear, very pale yellow solution. Silica gel was added and the solvent was removed under reduced pressure. Chromatography on silica gel eluting with 5-50-100% ethyl acetate in hexanes gave 7-chloro-3-(2-chlorobenzyl)-5-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one as a white solid (59% yield).

Provenance & Evidence