Benzoyl chloride → HCID 10054324, compound

Participants

Reaction Steps

To a solution of 41.4 mg (0.0834 mmole) of 5-n-butyl-2-(2-chlorophenyl)-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step B) in 1 ml of dry pyridine stirred at room temperature under argon was added 97 μl (117 mg, 0.836 mmole) of benzoyl chloride. The resulting solution was stirred at room temperature for 12 hours and then treated with saturated NaH2PO4 solution. The mixture was extracted 3× with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was flash chromatographed twice on silica gel (elution with 6-7% MeOH in CH2Cl2 containing 0.2-0.4% concd. NH4OH) to give 30 mg (60%) of the title compound as a white solid; satisfactory purity by TLC in 94:6:0.2 CH2Cl2 --MeOH-concd. NH4OH; mass spectrum (FAB) m/e 601 (M+1)+.

Provenance & Evidence