Stannous Chloride → 2,6 Dichloro-4-fluoro-phenylhydrazine hydrochloride

HRID 2261734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261734
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH2:10].[N:11]([O-])=O.[Na+].Cl[Sn]Cl>Cl.C(O)(C(F)(F)F)=O.O>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][NH2:11]

Komponenten

7

Edukt 3

HCID 24479Stannous ChlorideHCID 27740082,6-Dichloro-4-fluoroanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 866354612,6 Dichloro-4-fluoro-phenylhydrazine hydrochlorideAusbeute 156,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. solution of 2,6 Dichloro-4-fluorophenylamine (3.0 g, 16.6 mmol) in 12 M HCl (30 mL) and TFA (20 mL) is added slowly and dropwise NaNO2 (20 mmol, 1.37 mL) in water (6 mL). The reaction is stirred at 0° C. for 1 h. A solution of SnCl2 (5.74 g, 25.6 mmol) in 12 M HCl (16 mL) is added over 15 minutes. The ice bath is removed and the reaction is stirred for 18 h. The reaction is filtered and the solid is washed with isopropyl alcohol. The solid is dried to yield the title compound (3.0 g, 96%). LC-ES/MS m/e 194.0 (M+1)

Aufarbeitung

  1. customThe ice bath is removed
  2. stirringthe reaction is stirred for 18 h
  3. filtrationThe reaction is filtered
  4. washthe solid is washed with isopropyl alcohol
  5. customThe solid is dried

Quellen und Nachweise

ORD-Eintrag
ord-d98ade15bb1a4f60999dc962101ddbd2
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846960B2

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