HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → 4-(3,4-Bis(benzyloxy)-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,2,3-thiadiazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | ethyl N-[(Z)-[1-[3-nitro-4,5-bis(phenylmethoxy)phenyl]-2-[2-(trifluoromethyl)-3-pyridinyl]ethylidene]amino]carbamate | HCID 87588773 | — |
| Product | 4-(3,4-Bis(benzyloxy)-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,2,3-thiadiazole | HCID 68701536 | — |
Reaction Steps
A mixture of (Z)-ethyl 2-(1-(3,4-bis(benzyloxy)-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)ethylidene)hydrazinecarboxylate (0.388 g, 0.64 mmol), in thionyl chloride (2 mL) was refluxed until no more starting material was detected. Excess of solvent was removed and the residue was purified by chromatography over silica gel using a mixture of dichloromethane/ethanol as eluent. Homogeneous fractions were pooled and evaporated to afford 4-(3,4-bis(benzyloxy)-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,2,3-thiadiazole, 0.184 g (51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09446012B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-09e17e318ad14de29ab1e5b92df6c9de |
| Source note | uspto-grants-2016_09 |