HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-(2-{2-[(benzyloxy)methyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-2-(benzyloxy)acetamide | HCID 57781207 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | N-(2-{2-[(benzyloxy)methyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamide | HCID 57781286 | 23.5% |
Reaction Steps
N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-2-(benzyloxy)acetamide (280 mg, 0.732 mmol) and pyridinium p-toluenesulfonate (36.6 mg, 0.146 mmol) were heated under reflux in xylene (15 mL) for 2.5 hr. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=30/70→60/40) to give the title compound (62.8 mg, yield 23%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08895591B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-9cccf51263834da295c84d5a1ac841e1 |
| Source note | uspto-grants-2014_11 |