1-Iodonaphthalene → HCID 23067344, compound

HRID 460674Notes

Reaction equation

HRID 460674 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=3)[CH:15]=[C:14]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:32][CH:31]=3)[CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I[C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][CH:42]=1.C(=O)([O-])[O-].[K+].[K+].C1O[CH2:73][CH2:72]OCCOCCOCCOCCOC1>[Cu].C1(C)C=C(C)C=C(C)C=1>[C:36]([C:33]1[CH:34]=[CH:35][C:30]([N:29]([C:14]2[CH:15]=[C:16]([N:18]([C:49]3[C:50]4[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH:46]=[CH:47][CH:48]=3)[C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=3)[CH:17]=[C:12]([N:11]([C:2]3[C:72]4[C:73](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:6]=[CH:5][CH:1]=3)[C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][CH:9]=3)[CH:13]=2)[C:41]2[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:44]=[CH:43][CH:42]=2)=[CH:31][CH:32]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 70041-IodonaphthaleneHCID 11430Potassium CarbonateHCID 2855718-Crown-62×HCID 23067346HCID 23067346, compound

Product 1

HCID 23067344HCID 23067344, compoundYield 124.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7947MesityleneSolvent

Procedure

2.6 g of 1,3,5-tris(p-tert.-butylphenylamino)benzene, 6.4 g of 1-iodonaphthalene, 6.9 g of potassium carbonate, 1.0 g of copper powder, 0.7 g of 18-crown-6 (or 1,4,7,10,13,16-hexaoxacyclo-octadecane) and 20 mL of mesitylene were placed in a 100 mL capacity flask and the reaction was carried out at a temperature of 170° C. for 16.5 hours under a nitrogen atmosphere. After the reaction, the resultant reaction mixture was extracted with toluene and the toluene solution was subjected to silica gel chromatography to fractionate the reaction product. The reaction product was then purified by recrystallization and then by sublimation to provide 2.8 g of the desired 1,3,5-tris(N-(p-tert.-butylphenyl)-N-(1-naphthyl)amino)-benzene. The yield was 62%.

Workup

  1. customAfter the reaction
  2. customthe resultant reaction mixture
  3. extractionwas extracted with toluene
  4. customThe reaction product was then purified by recrystallization

Sources & evidence

ORD record
ord-6650d9ebaec1423e868ae894e288b150
Source dataset
uspto-grants-2007_03
Patent number
US07196224B2

Reaction notes

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