HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → (E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | O-(Tetrahydropyran-2-yl)hydroxylamine | HCID 5142091 | — |
| Reactant | (E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid | HCID 68526317 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | (E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide | HCID 86621698 | — |
Reaction Steps
A mixture of 6.1 g (E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid with 300 ml DMF and 2.6 g HOBt.H2O and 24.0 ml triethylamine is stirred at ambient temperature for 0.5 h. Then 9.8 g EDC.HCL is added and the suspension is stirred again at ambient temperature for 0.5 h. After that 2.0 g O-(tetrahydro-2H-pyran-2-yl)hydroxylamine are added and the suspension is stirred at ambient temperature for 24 h. The DMF is evaporated and the residue is extracted with ethyl acetate and water. The organic layer is dried over sodium sulfate. The title compound is isolated by flash chromatography. By this method 6.3 g of a yellow foam are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815855B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-09a5b9688c974dbeab3f385b65cfce04 |
| Source note | uspto-grants-2014_08 |