HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 1-(2-(4-isopropyl-4H-1,2,4-triazol-3-yl)phenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-[4-(propan-2-yl)-4H-1,2,4-triazol-3-yl]aniline | HCID 62695846 | — |
| Reactant | 3-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole | HCID 118590165 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | 1-(2-(4-isopropyl-4H-1,2,4-triazol-3-yl)phenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea | HCID 118675106 | 20.7% |
Reaction Steps
3-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (WO 2011/017513) (0.088 g, 0.24 mmol), 2-(4-isopropyl-4H-1,2,4-triazol-3-yl)aniline (0.080 g, 0.40 mmol), and cesium carbonate (0.16 g, 0.50 mmol) in isopropyl alcohol (1.2 mL) was stirred at room temperature overnight. The reaction was diluted with water and extracted with ethyl acetate. The organic layers were dried over sodium sulfate, filtered and concentrated. The residue was loaded onto Celite® cartridge and purified by flash chromatography using 0-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes as eluent to provide the title compound as a yellow solid (0.028 g, 20%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09445594B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-09657edde74e463b9c114b54dc01c44b |
| Source note | uspto-grants-2016_09 |