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

HRID 31736

Reaction equation

HRID 31736 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6344DichloromethaneSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-eb6ad7a0b9d2406aad6f0d5931f4fdb6
Source dataset
uspto-grants-2008_09
Patent number
US07425723B2

Linked notes

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