Reaction #64526

Reaction equation

2-chlorobenzoic acid

CDI

5-n-butyl-2,4-dihydro-2-(4-nitro-2-trifluoromethyl)phenyl-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

5-n-Butyl-2,4-dihydro-2-[4-nitro-2-(trifluoromethyl)phenyl]-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

DBU

→

title compound

5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-2-[4-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Conditions

Procedure

The title compound was prepared from 2-chlorobenzoic acid (2.0 equivalents), CDI (2.0 equiv), 5-n-butyl-2,4-dihydro-2-(4-nitro-2-trifluoromethyl)phenyl-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step C) (1.0 eq), and DBU (2.0 equiv) according to the procedure of Example 51, to give a 43% yield of the desired material after flash chromatography, as a glassy solid, mp 179°-181° C., homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 714 (M+1)+.

Source