HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → N-{5-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Acetylamino-4-chlorophenol | HCID 95258 | — |
| Reactant | Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester | HCID 146490 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-{5-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide | HCID 86601480 | 92.3% |
Reaction Steps
A mixture of N-(5-chloro-2-hydroxyphenyl)acetamide (500 mg, 2.69 mmol), (2S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate (697 mg, 2.69 mmol) and Cs2CO3 (1.04 g, 3.22 mmol) in DMF (10 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum ether) to give the subtitled compound (600 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07449475B2 |
| Source dataset | uspto-grants-2008_11 |
| ORD ID | ord-ba1e445f47844faaa2ea1eba40902c38 |
| Source note | uspto-grants-2008_11 |