3-Chloropropionyl chloride → 1-(4-Trifluoromethoxyphenyl)-pyrazolidin-3-one

HRID 1192782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192782
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.Cl[CH2:16][CH2:17][C:18](Cl)=[O:19].CCN(C(C)C)C(C)C>C1COCC1>[F:2][C:3]([F:13])([F:14])[O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:17][C:18](=[O:19])[NH:12]2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 693643-Chloropropionyl chlorideHCID 81531DiisopropylethylamineHCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochloride

Produkt 1

HCID 669570351-(4-Trifluoromethoxyphenyl)-pyrazolidin-3-oneAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  1. customThe compound was prepared
  2. filtrationThe solution was then filtered
  3. concentrationconcentrated to dryness
  4. custompurified via chromatography (2:2:1, hexane:EtOAc:acetone)

Quellen und Nachweise

ORD-Eintrag
ord-9939b6b3e41949748bea1a9b23d7f922
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680269B2

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