4-Chloroaniline → HCID 178449876, Verbindung

HRID 75484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75484
[C:1](#[N:5])[CH2:2][CH2:3][CH3:4].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1.O>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:1](=[NH:5])[CH2:2][CH2:3][CH3:4])=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 78124-Chloroaniline2×HCID 8008Butyronitrile2×HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 178449876HCID 178449876, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a solution of butyronitrile (compound 2, 7.5 mL, 86.2 mmol), AlCl3 in toluene was added 4-chloroaniline (compound 1, 10.0 g, 78.4 mmol). The reaction mixture was stirred at 115° C. for 5 hrs. The mixture was diluted with water (200 mL) and extracted with EtOAc (200 mL) The aqueous layer was neutralized with saturated NaHCO3 (500 mL) and extracted with EtOAc (300 mL×2). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The obtained product (9.2 g, pale brown solid) was used for the next step without purification.

Aufarbeitung

  1. extractionextracted with EtOAc (200 mL) The aqueous layer
  2. extractionextracted with EtOAc (300 mL×2)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained product (9.2 g, pale brown solid) was used for the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-5d9fdc9310e449abab4ec5622bb74e20
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835436B2

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