HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 69520328, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dabco | HCID 9237 | — |
| Reactant | Carbamic chloride, N-methyl-N-phenyl- | HCID 77969 | — |
| Reactant | HCID 178445144 | HCID 178445144 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Heptane | HCID 8900 | — |
| Product | HCID 69520328 | HCID 69520328 | 79.1% |
Reaction Steps
A solution of N-(6-hydroxy-pyridin-3-yl)-3,3-dimethyl-butyramide (0.42 g, 2.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.37 g, 2.20 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.25 g, 2.20 mmol) in tetrahydrofuran (20 mL) was stirred at room temperature for 2.5 hours. Water was added and the solution was extracted three times with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated in vacuo. The residue was redissolved in ethyl acetate and the solution was filtered over a short pad of silicagel. Evaporation of the solvent and crystallisation of the solid from ethyl acetate:heptane yielded the title compound (0.54 g, 79% yield) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07279470B2 |
| Source dataset | uspto-grants-2007_10 |
| ORD ID | ord-17b24aa2297e4281a8f500637c933300 |
| Source note | uspto-grants-2007_10 |