HuagongsheHuagongshe Chemistry Print Report · For research reference only
(Isocyanoimino)triphenylphosphorane → 8-Bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (Isocyanoimino)triphenylphosphorane | HCID 11266621 | — |
| Reactant | 8-Bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylic acid | HCID 57900166 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 8-Bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene | HCID 57900185 | — |
Reaction Steps
To a solution of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (22.2 g, 68.1 mmol) in THF (360 mL) was added (isocyanoimino)triphenylphosphorane (20.6 g, 68.1 mmol) portionwise over 1 hour. The resultant mixture was stirred at RT for 18 hours before being concentrated in vacuo and triturated with 1:1 DCM/cyclohexane (200 mL). The title compound was collected by filtration as a yellow solid (14.5 g, 61%). LCMS: RT=4.03 min, M+H+=350/352.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09175009B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-169990f3f08e484286a3bee301e069e1 |
| Source note | uspto-grants-2015_11 |