Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Phenol | HCID 996 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Nitrothiophene-2-carbonitrile | HCID 519294 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23130496 | HCID 23130496 | 72.2% |
Reaction Steps
5-Nitro-thiophene-2-carbonitrile(1.5 g, 9.7 mmol), phenol (1.8 g, 19.4 mmol) and potassium carbonate(4.0 g, 29.1 mmol) were suspended in dimethylsulfoxide (20 mL), and the mixture was stirred for 50 minutes at 60° C., followed by further stirring overnight at room temperature. Water and ethyl acetate were added to the reaction mixture, which was then partitioned, the organic layer was washed 4 times with water, then, NH silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (hexane, then hexane:ethyl acetate=20:1, then 10:1), and the title compound (1.4 g, 7.0 mmol, 72.1%) was obtained as a pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07932272B2 |
|---|
| Source dataset | uspto-grants-2011_04 |
|---|
| ORD ID | ord-33bcbbf33ecb4d0bbad657ee50f66f17 |
|---|
| Source note | uspto-grants-2011_04 |
|---|