HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → N-[5-(4-Hydroxy-phenylsulfanyl)-2-methyl-4-nitro-phenyl]-2-phenyl-acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Mercaptophenol | HCID 240147 | — |
| Reactant | N-(5-chloro-2-methyl-4-nitrophenyl)-2-phenylacetamide | HCID 2907847 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-[5-(4-Hydroxy-phenylsulfanyl)-2-methyl-4-nitro-phenyl]-2-phenyl-acetamide | HCID 67041085 | 72% |
Reaction Steps
The product from Example 265A (0.305 g, 1.0 mmol), 4-mercaptophenol (0.151 g, 1.2 mmol, 1.2 eq) and cesium carbonate (0.782 g, 2.4 mmol, 2.4 eq) in dimethyl formamide (10 mL) was heated at 110° C. for 2 h, cooled to room temperature, and poured over ice water (100 mL). This mixture was extracted with ethyl acetate (3×150 mL) and the combined organic phases were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was purified by chromatography on silica gel eluting with 1:1 hexane/ethyl acetate to provide the title compound as a yellow solid (0.282 g, 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07910595B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-bd57b1622be445fcb574be2ec28d0f8d |
| Source note | uspto-grants-2011_03 |