4-Fluorophenylhydrazine hydrochloride → HCID 59161212, Verbindung

HRID 545500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545500
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.O=[C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:13]1>Cl>[F:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:23])[CH:20]([CH3:21])[CH3:22])[CH2:14][C:13]2=1

Komponenten

4

Edukt 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

Produkt 1

HCID 59161212HCID 59161212, VerbindungAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Combine p-fluorophenylhydrazine hydrochloride (5.00 g, 30.7 mmol) and N-(4-oxo-cyclohexyl)isobutyramide (5.64 g, 30.7 mmol) in ethanolic HCl (125 mL) and heat at reflux under nitrogen for 18 h. Concentrate the reaction in vacuo to remove most of the EtOH, dilute with water and extract with EtOAc. Wash the EtOAc extracts with water and brine, dry over Na2SO4, and evaporate to give 7.1 g (56%) of a beige solid. MS (ES): m/z 275 (M+1); 1H NMR(DMSO-d6): δ 10.79 (s, 1H, NH), 7.81 (d, 1H, J=7.5 Hz), 7.19 (dd, 1H, J=8.6, 4.6 Hz), 7.07 (d, 1H, J=10.1 Hz), 6.79 (dt, 1H, J=8.9, 1.8 Hz), 4.00 (m, 1H), 2.85 (dd, 1H, J=15.0, 5.3 Hz), 2.76 (m, 2H), 2.39 (m, 2H), 1.93 (m, 1H), 1.75 (m, 1H), 0.99 (d, 6H, J=6.6 Hz).

Aufarbeitung

  1. temperatureat reflux under nitrogen for 18 h
  2. concentrationConcentrate
  3. customthe reaction in vacuo
  4. customto remove most of the EtOH
  5. additiondilute with water
  6. extractionextract with EtOAc
  7. washWash the EtOAc
  8. dry with materialdry over Na2SO4
  9. customevaporate

Quellen und Nachweise

ORD-Eintrag
ord-b0ff8d24e73042a5ba5bd6ac7d073c25
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935722B2

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