HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carboxamide → 1-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carboxamide | HCID 46781618 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Thionyl Chloride | HCID 24386 | — |
| Product | 1-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carbonitrile | HCID 18761817 | — |
Reaction Steps
A suspension of 1-(4-fluoro-phenyl)-3-oxo-1,3-dihydro-isobenzofuran-5-carboxylic acid amide (13.6 g, 0.05 mole) in thionyl chloride (40 mL) and DMF (0.25 mL) was heated at reflux for 2 hours. The thionyl chloride was then evaporated, and the residue was dissolved in hot IPA (100 mL). On cooling, crystals of the title compound were formed. Yield: 7.8 g (62%). 1H NMR (d6-DMSO): δ 6.87 (s, 1H), 7.26 (t, 2H), 7.42 (dd, 2H), 7.58 (d, 1H), 8.18 (dd, 1H), 8.48 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06660873B2 |
| Source dataset | uspto-grants-2003_12 |
| ORD ID | ord-ba1780a7565249908ba0eea4a77dd709 |
| Source note | uspto-grants-2003_12 |