HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Chloropropionyl chloride → 1-(4-Trifluoromethoxyphenyl)-pyrazolidin-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Chloropropionyl chloride | HCID 69364 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-(Trifluoromethoxy)phenylhydrazine hydrochloride | HCID 2777328 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(4-Trifluoromethoxyphenyl)-pyrazolidin-3-one | HCID 66957035 | 37% |
Reaction Steps
The compound was prepared according to Rees and Tsoi Chem. Commun. 2000, 415. A suspension of (4-trifluoromethoxyphenyl)-hydrazine hydrochloride (300 mg, 1.32 mmol, 1.00 eq), 3-chloropropionyl chloride (167 mg, 1.32 mmol, 1.00 eq), and PS-DIEA (1.30 grams (g), 5.28 mmol, 4.00 eq) in THF (20 mL) was stirred at ambient temperature for 12 h. The solution was then filtered, concentrated to dryness, and purified via chromatography (2:2:1, hexane:EtOAc:acetone) to afford the desired intermediate (120 mg, 37%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680269B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-9939b6b3e41949748bea1a9b23d7f922 |
| Source note | uspto-grants-2014_03 |