HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chlorobenzoic Acid → 5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chlorobenzoic Acid | HCID 8374 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 5-n-Butyl-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-2-[5-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one | HCID 19939372 | — |
| Product | 5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one | HCID 19939365 | 86% |
Reaction Steps
By the procedure of Example 51, 5-n-butyl-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-2-[5-nitro-2-(trifluoromethyl)-phenyl]-3H-1,2,4-triazol-3-one (from Step E) was reacted with 2-chlorobenzoic acid (3 equivalents), CDI (3 equiv), and DBU (3 equiv). Flash chromatography of the crude product on silica gel afforded an 86% yield of the title compound as a foam; homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 732 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05411980 |
| Source dataset | uspto-grants-1995_05 |
| ORD ID | ord-a3ba6739d1484bd6bf54e1da27d3fd77 |
| Source note | uspto-grants-1995_05 |