Sodium hydride → 10-(4,6-Bisbiphenyl-3-yl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275923Notes

Reaction equation

HRID 2275923 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2=[CH:11][C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4.[H-].[Na+].[C:25]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[N:36]=[C:35]([C:37]3[CH:38]=[C:39]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:40]=[CH:41][CH:42]=3)[N:34]=[C:33](Cl)[N:32]=2)[CH:26]=1>CN(C)C=O.C1COCC1>[C:39]1([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:40]=[CH:41][CH:42]=[C:37]([C:35]2[N:36]=[C:31]([C:27]3[CH:26]=[C:25]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[CH:30]=[CH:29][CH:28]=3)[N:32]=[C:33]([N:13]3[C:12]4[CH:11]=[C:10]5[C:2]([CH3:22])([CH3:1])[C:3]6[C:8]([C:9]5=[CH:21][C:20]=4[C:19]4[C:14]3=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:7][CH:6]=[CH:5][CH:4]=6)[N:34]=2)[CH:38]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 582991182,4-Di([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazineHCID 665852047,7-Dimethyl-5,7-dihydroindeno[2,1-b]carbazole

Product 1

HCID 6679766510-(4,6-Bisbiphenyl-3-yl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

18.6 g (64.6 mmol) of 12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]-fluorene are dissolved in 400 ml of dimethylformamide under a protective-gas atmosphere, and 3.1 g of 60% NaH in mineral oil (77.5 mmol) are added. After 1 h at room temperature, a solution of 2,4-bisbiphenyl-3-yl-6-chloro-1,3,5-triazine (32.6 g, 64.6 mmol) in 100 ml of THF is added dropwise. The reaction mixture is stirred at room temperature for 12 h. After this time, the reaction mixture is poured onto ice and extracted three times with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum, the purity is 99.9%. Yield: 41.5 g (61 mmol), 80% of theory.

Workup

  1. additionare added
  2. additionAfter this time, the reaction mixture is poured onto ice
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. extractionThe residue is extracted with hot toluene
  7. customrecrystallised from toluene

Sources & evidence

ORD record
ord-92076b4d5a754d96852a1a8c3252cce6
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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