1-Iodonaphthalene → HCID 11411696, compound

HRID 460673Notes

Reaction equation

HRID 460673 reaction equation
[C:1]1([CH3:30])[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[CH:11]=[C:10]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)[CH:9]=2)=[CH:3][CH:2]=1.I[C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+].C1O[CH2:64][CH2:63]OCCOCCOCCOCCOC1.[C:66]1([CH3:74])[CH:71]=[C:70](C)[CH:69]=[C:68](C)[CH:67]=1>[Cu]>[CH3:30][C:1]1[CH:6]=[CH:5][C:4]([N:7]([C:8]2[CH:13]=[C:12]([N:14]([C:68]3[C:67]4[C:66](=[CH:74][CH:20]=[CH:15][CH:16]=4)[CH:71]=[CH:70][CH:69]=3)[C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[CH:11]=[C:10]([N:22]([C:13]3[C:63]4[C:64](=[CH:3][CH:2]=[CH:1][CH:6]=4)[CH:10]=[CH:9][CH:8]=3)[C:23]3[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=3)[CH:9]=2)[C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 70041-IodonaphthaleneHCID 7947MesityleneHCID 11430Potassium CarbonateHCID 2855718-Crown-62×HCID 11749735HCID 11749735, compound

Product 1

HCID 11411696HCID 11411696, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

2.0 g of 1,3,5-tris(p-tolylamino)benzene, 6.4 g of 1-iodo-naphthalene, 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-hexaoxacyclooctadecane) and 15 mL of mesitylene were placed in a 100 mL capacity glass flask and the reaction was carried out at a temperature of 170° C. for 18 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 2.2 g of the desired 1,3,5-tris(N-(p-methylphenyl)-N-(1-naphthyl)-amino)benzene (p-MTPNAB). The yield was 57%.

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-57ca527e85804535843ffe788b79f221
Source dataset
uspto-grants-2007_03
Patent number
US07196224B2

Reaction notes

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