Potassium Carbonate → 1,3,5-Tris(n-(4-biphenylyl)-n-(1-naphthyl)amino)benzene

HRID 917001Notes

Reaction equation

HRID 917001 reaction equation
[C:1]1([NH:11][C:12]2[CH:17]=[C:16]([NH:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)[CH:15]=[C:14]([NH:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)[CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.I[C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:43][CH:42]=1.C(=O)([O-])[O-].[K+].[K+].C1O[CH2:75][CH2:74]OCCOCCOCCOCCOC1>[Cu].C1(C)C=C(C)C=C(C)C=1>[C:44]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:45]=[CH:46][C:41]([N:11]([C:12]2[CH:13]=[C:14]([N:29]([C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)[C:50]3[CH:51]=[CH:52][C:47]([C:44]4[CH:45]=[CH:46][CH:41]=[CH:42][CH:43]=4)=[CH:48][CH:49]=3)[CH:15]=[C:16]([N:18]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)[C:1]3[CH:10]=[CH:5][C:4]([C:75]4[CH:74]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:3][CH:2]=3)[CH:17]=2)[C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[CH:42][CH:43]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 153224-IodobiphenylHCID 2855718-Crown-62×HCID 231397241,3,5-Tris(l-naphthylamino)benzene

Product 1

HCID 231397251,3,5-Tris(n-(4-biphenylyl)-n-(1-naphthyl)amino)benzeneYield 110.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7947MesityleneSolvent

Procedure

2.0 g of 1,3,5-tris(1-naphthylamino)benzene, 5.0 g of 4-iodobiphenyl, 3.7 g of potassium carbonate, 2 g of copper powder, 0.3 g of 18-crown-6 (or 1,4,7,10,13,16-hexaoxacyclooctadecane) and 10 mL of mesitylene as a reaction solvent were placed in a 100 mL capacity glass flask and the reaction was carried out at a temperature of 170° C. for 17 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 from a mixed solvent of toluene/hexane and then by sublimation to provide 1.2 g of the desired 1,3,5-tris(N-(4-biphenylyl)-N-(1-naphthyl)amino)benzene (TBNAB). The yield was 32%.

Workup

  1. customAfter the reaction
  2. customthe resultant reaction mixture
  3. extractionwas extracted with toluene
  4. customThe reaction product was then purified by recrystallization from a mixed solvent of toluene/hexane

Sources & evidence

ORD record
ord-8fc0f2e29120456e8994531a6e7e75d7
Source dataset
uspto-grants-2007_09
Patent number
US07271291B2

Reaction notes

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