Potassium Carbonate → 1,3,5-Tris(4-aminophenyl)benzene

HRID 1650263Notes

Reaction equation

HRID 1650263 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[CH:11]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[CH:9]=2)=[CH:4][CH:3]=1.I[C:29]1[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].C1O[CH2:58][CH2:57]OCCOCCOCCOCCOC1>[Cu].ClC1C=CC=CC=1Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[CH:13]=2)=[CH:4][CH:3]=1.[C:31]1([CH3:35])[CH:32]=[CH:33][CH:34]=[C:29]([N:1]([C:22]2[CH:23]=[C:57]([CH3:58])[CH:9]=[CH:10][CH:21]=2)[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[C:10]([C:21]4[CH:26]=[CH:25][C:24]([N:27]([C:29]5[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=5)[C:29]5[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=5)=[CH:23][CH:22]=4)[CH:11]=[C:12]([C:14]4[CH:19]=[CH:18][C:17]([N:20]([C:7]5[CH:6]=[C:5]([CH3:8])[CH:4]=[CH:3][CH:2]=5)[C:16]5[CH:15]=[C:14]([CH3:12])[CH:19]=[CH:18][CH:17]=5)=[CH:16][CH:15]=4)[CH:13]=3)=[CH:4][CH:3]=2)[CH:30]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 122683-IodotolueneHCID 2855718-Crown-6HCID 120588131,3,5-Tris(4-aminophenyl)benzene

Product 2

HCID 120588131,3,5-Tris(4-aminophenyl)benzeneHCID 16180234HCID 16180234, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

1,3,5-tris(4-aminophenyl)benzene was prepared as described above in the preparation of compound 1. A mixture of 3 g of 1,3,5-tris(4-aminophenyl)-benzene, 22.2 g of m-iodotoluene, 5.9 g of potassium carbonate, 0.2 g of 18-crown-6 crown ether, 2.2 g of copper bronze and 40 ml of orthodichlorobenzene was flushed with argon and then the whole apparatus placed under vacuum. The mixture was then refluxed under argon for 120 hours. The reaction mixture was then filtered hot and the filtrate evaporated to dryness. High boiling point petroleum ether was then added and the product crystallized slowly in a deep freeze. It was then filtered off, dissolved in dichloromethane, precipitated with methanol and the precipitate, after drying, purified by preparative chromatographically using a 7:1 mixture of dichloromethane and n-hexane as the eluent. The 1,3,5-tris-(4-di-m -tolylaminophenyl)benzene produced had a melting point of 269.6° C.

Workup

  1. customwas flushed with argon
  2. temperatureThe mixture was then refluxed under argon for 120 hours
  3. filtrationThe reaction mixture was then filtered hot
  4. customthe filtrate evaporated to dryness
  5. additionwas then added
  6. customthe product crystallized slowly in a deep freeze
  7. filtrationIt was then filtered off
  8. dissolutiondissolved in dichloromethane
  9. customprecipitated with methanol
  10. customthe precipitate, after drying
  11. custompurified by preparative
  12. additiona 7:1 mixture of dichloromethane and n-hexane as the eluent

Sources & evidence

ORD record
ord-91dea1c204424bebb57043faa6ec854c
Source dataset
uspto-grants-1990_05
Patent number
US04923774

Reaction notes

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