HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 6-Chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | N-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamide | HCID 66880038 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 6-Chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazole | HCID 66881760 | 69.3% |
Reaction Steps
To a mixture of 1.01 g of N-[4-chloro-2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 10 ml of tetrahydrofuran and 0.92 g of triphenylphosphine, 1.53 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature, and the reaction mixture was stirred for two hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant crystals washed with methanol to give 0.66 g of 6-chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 80”).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609705B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-38688750df4649b3a52c5be15cdb24a7 |
| Source note | uspto-grants-2013_12 |