Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 2(3H)-Oxazolone, 5-methyl-4-phenyl- | HCID 12307000 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 23143330 | HCID 23143330 | 49.1% |
Reaction Steps
To a suspension of 5-methyl-4-phenyl-1,3-oxazol-2(3H)-one (430 mg, 2.45 mmol) in phosphorus oxychloride (2.36 g, 14.7 mmol) was added pyridine (194 mg, 2.45 mmol) and the mixture was stirred at 120° C. for 2 hr. The reaction mixture was diluted with acetonitrile and added dropwise to water (about 30° C.). The organic materials were extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (233 mg, yield 49%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07585880B2 |
|---|
| Source dataset | uspto-grants-2009_09 |
|---|
| ORD ID | ord-d07c2186d94441beb2a75acc0f474251 |
|---|
| Source note | uspto-grants-2009_09 |
|---|