Hydrazine → HCID 178509108, Verbindung

HRID 1058058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058058
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:10]#[N:11])=[CH:4][CH:3]=1.P(Cl)(Cl)Cl.[NH2:23][NH2:24]>C(#N)C>[NH2:11][C:10]1[NH:24][N:23]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 9321HydrazineHCID 24387Phosphorus trichlorideHCID 220374773-(4-Chlorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile

Produkt 1

HCID 178509108HCID 178509108, VerbindungAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 3-(4-chlorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile (3.50 g, 13.6 mmol) in 40 mL acetonitrile and phosphorous trichloride (14.2 ml, 163 mmol) was stirred at 100° C. for 5 hours. The reaction mixture was concentrated in vacuo, and the residue taken up in toluene and concentrated again. The residue was then taken up in ethanol (150 mL) and treated with anhydrous hydrazine (1.71 mL, 54.4 mmol). The reaction mixture was heated to reflux for 3 hours, cooled, and concentrated in vacuo. The residue was triturated with a mixture of ethanol and dichloromethane (1:4), and filtered. The solid was washed with the ethanol/dichloromethane mixture, and dried to give 5-amino-3-(4-chlorophenyl)-4-(pyridin-4-yl)-pyrazole (2.0 g, 54%): m.p. >300° C. 1H NMR (DMSO/300 MHz) δ 8.40 (d, 2H), 7.40 (d, 2H), 7.29 (d, 2H), 7.11 (d, 2H), 5.05 (s, 2H). ESLRMS m/z 271 (M+H). ESHRMS m/z 271.0752 (M+H, C14H11N4Cl requires 271.0750).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. concentrationconcentrated again
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 3 hours
  5. temperaturecooled
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with a mixture of ethanol and dichloromethane (1:4)
  8. filtrationfiltered
  9. washThe solid was washed with the ethanol/dichloromethane mixture
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-67db8272c3ce4089ab214c18d547b85b
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514977B1

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