2-Chloro-4,6-diphenyl-1,3,5-triazine → 7-Dibenzofuran-4-yl-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275951Notes

Reaction equation

HRID 2275951 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:14]2[CH:15]=[C:16]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22]2[CH:21]=[C:20]4[C:27]([CH3:35])([CH3:34])[C:28]5[C:33]([C:19]4=[CH:18][C:17]3=2)=[CH:32][CH:31]=[CH:30][CH:29]=5)=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:39]1[N:44]=[C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:42]=[C:41]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:40]=1>CN(C)C=O>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:14]2[CH:15]=[C:16]3[C:24](=[CH:25][CH:26]=2)[N:23]([C:39]2[N:44]=[C:43]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:42]=[C:41]([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[N:40]=2)[C:22]2[CH:21]=[C:20]4[C:27]([CH3:35])([CH3:34])[C:28]5[C:33]([C:19]4=[CH:18][C:17]3=2)=[CH:32][CH:31]=[CH:30][CH:29]=5)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 24758Sodium hydrideHCID 667975987-Dibenzofuran-4-yl-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Product 1

HCID 667978447-Dibenzofuran-4-yl-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

16.6 g (58.78 mmol) of 7-dibenzofuran-4-yl-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene are dissolved in 225 ml of dimethylformamide under a protective-gas atmosphere, and 2.8 g of 60% NaH in mineral oil (70 mmol) are added. After 1 h at room temperature, a solution of 2-chloro-4,6-diphenyl-1,3,5-triazine (18.6 g, 66.2 mmol) in 75 ml of dimethylformamide 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 dichloromethane/isopropanol and finally sublimed in a high vacuum, the purity is 99.9%. The yield is 18.3 g (27 mmol, 45.7%).

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 dichloromethane/isopropanol

Sources & evidence

ORD record
ord-100adca25c5549aea57c405d9bb73414
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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