HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoyl isothiocyanate → N-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole-3-carbonothioyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoyl isothiocyanate | HCID 68284 | — |
| Reactant | 2-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole | HCID 86604831 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole-3-carbonothioyl)benzamide | HCID 86608769 | 99.4% |
Reaction Steps
To a solution of 2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole (1.00 g, 2.79 mmol) in 20 mL of anhydrous THF was added benzoyl isothiocyanate (0.45 mL, 3.34 mmol). The reaction mixture was stirred overnight at reflux, then cooled and concentrated in vacuo. The residue was purified by flash column chromatography (5-35% ethyl acetate/hexanes) to afford the desired product as a yellow gum (1.45 g, 54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08268871B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-18898d1c85aa4be08dfdbfc6d798af18 |
| Source note | uspto-grants-2012_09 |