Acetylacetone → HCID 178468338, Verbindung

HRID 1895207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1895207
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N:10]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:19]([CH2:22][C:23](=[O:25])[CH3:24])(=[O:21])[CH3:20]>C(O)(=O)C.Cl.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:10]=[C:22]([C:23](=[O:25])[CH3:24])[C:19](=[O:21])[CH3:20])=[C:4]([F:9])[CH:3]=1

Komponenten

8

Edukt 4

HCID 31261AcetylacetoneHCID 938984-Chloro-2-fluoroanilineHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Produkt 1

HCID 178468338HCID 178468338, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-chloro-2-fluoroaniline (1 g, 6.87 mmol) in 9.8 mL of acetic acid and 1.6 mL of concentrated hydrochloride solution, sodium nitrite (568 mg, 8.24 mmol) in 2.6 mL of water was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 h. Then to the reaction mixture were added sodium acetate (1.69 g, 20.6 mmol) and acetylacetone (893 mg, 8.93 mmol). The mixture was stirred at room temperature for 2 h, filtered, washed with water, EtOH/H2O (1/1) and hexane, and dried to give the title compound (1 g, 57% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.49 (s, 3H), 2.60 (s, 3H), 7.15-7.25 (m, 2H), 7.69 (t, J=8.4 Hz, 1H), 14.64 (s, 1H).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. filtrationfiltered
  3. washwashed with water, EtOH/H2O (1/1) and hexane
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9532745121ef4c44bdbaaac5a95f74f7
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513251B2

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