HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate | HCID 59625786 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylate | HCID 59626027 | 55% |
Reaction Steps
Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate 9dd (7.4 mmol, 1.2 g crude) and 1.3 g (7.5 mmol) of p-toluenesulfonic acid was refluxed in 10 mL of xylene overnight. After cooling saturated NaHCO3 was added and the resulting mixture was extracted with EtOAc. The organic solvent was evaporated to give 1.1 g (55%) of methyl 2-(4-fluorophenyl)benzo[d]oxazole-4-carboxylate, 9ee. MS m/z (M+H+) 272.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08604017B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-4f7344602c514290aedd12b72cdf3215 |
| Source note | uspto-grants-2013_12 |