Potassium Carbonate → Bis(4-chlorophenyl)(4-octylphenyl)amine

HRID 31736

Reaktionsgleichung

Reaktionsgleichung von HRID 31736
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1O[CH2:32][CH2:31]OCCOCCOCCOCCOC1.C([O-])([O-])=O.[K+].[K+].[Cl:40][C:41]1[CH:46]=[CH:45][C:44](I)=[CH:43][CH:42]=1>ClCCl.[Cu].ClC1C=CC=CC=1Cl>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([N:13]([C:32]2[CH:31]=[CH:46][C:41]([Cl:40])=[CH:42][CH:43]=2)[C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)=[CH:43][CH:42]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 2855718-Crown-6HCID 853464-Octylaniline

Produkt 1

HCID 58918513Bis(4-chlorophenyl)(4-octylphenyl)amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 72391,2-DichlorobenzeneLösungsmittel

Versuchsvorschrift

4-Octylaniline (5.00 g, 244.4 mmol), 18-crown-6 (1.29 g, 4.9 mmol), K2CO3 (27.64 g, 194.8 mmol), 1-chloro-4-iodobenzene (14.51 g, 60.9 mmol, copper (6.19 g, 97.4 mmol), and 1,2-dichlorobenzene (100 mL) were added in a 250 mL flask with a condenser connected to a Dean Stark apparatus. The mixture was heated to reflux for 24 hours under argon. The reaction mixture was then cooled to room temperature, diluted with dichloromethane, and filtered. After removal of solvent by distillation, the product was purified using silica gel column chromatography using hexane as eluant. The yield was 4.18 g (40.3%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 hours under argon
  3. filtrationfiltered
  4. customAfter removal of solvent
  5. distillationby distillation
  6. customthe product was purified

Quellen und Nachweise

ORD-Eintrag
ord-eb6ad7a0b9d2406aad6f0d5931f4fdb6
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425723B2

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