HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrothiopyran-4-one → N-(Tetrahydrothiopyran-4-yl)-4-trifluoromethylnicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrothiopyran-4-one | HCID 66173 | — |
| Reactant | Tetrahydrothiopyran-4-ylamine | HCID 418807 | — |
| Reactant | 4-Trifluoromethylnicotinoyl chloride | HCID 11790465 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-(Tetrahydrothiopyran-4-yl)-4-trifluoromethylnicotinamide | HCID 11680848 | 51.3% |
Reaction Steps
Analogously to Example A, equimolar amounts of 4-aminotetrahydrothiopyran (prepared from tetrahydrothiopyran-4-one via the corresponding oxime and subsequent reduction with lithium aluminum hydride in tetrahydrofuran) and 4-trifluoromethylnicotinoyl chloride were reacted in the presence of triethylamine. This gave, after silica gel chromatography (ethyl acetate), the amide as a colorless solid of melting point 161-163° C. (Yield 51.3% of theory).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07332509B2 |
| Source dataset | uspto-grants-2008_02 |
| ORD ID | ord-6274030001d644ee81a1b28d2f477363 |
| Source note | uspto-grants-2008_02 |