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

HRID 2275919Notes

Reaction equation

HRID 2275919 reaction equation
[CH3:1][C:2]1([CH3:28])[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][C:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:16][CH:15]=4.[H-].[Na+].Cl[C:32]1[N:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:35]=[C:34]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:33]=1>CN(C)C=O>[C:44]1([C:34]2[N:35]=[C:36]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:37]=[C:32]([N:13]3[C:12]4[CH:11]=[C:10]5[C:2]([CH3:28])([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]=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=4)=[CH:7][CH:6]=[CH:5][CH:4]=6)[N:33]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 24758Sodium hydrideHCID 6679746212,12-Dimethyl-7-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Product 1

HCID 6679759610-(4,6-Diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-7-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

10 g (27.7 mmol) of 12,12-dimethyl-7-phenyl-10,12-dihydro-10-azaindeno-[2,1-b]fluorene are dissolved in 275 ml of dimethylformamide under a protective-gas atmosphere, and 1.45 g of NaH, 60% in mineral oil (36 mmol), are added. After 1 h at room temperature, a solution of 2-chloro-4,6-diphenyl-1,3,5-triazine (8.2 g, 30.5 mmol) in 75 ml of dimethylformamide is added dropwise. The reaction mixture is then 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. The yield is 14.7 g (24.9 mmol, 90%).

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

Sources & evidence

ORD record
ord-48697e7d96a14110af314f3d1d8dea3e
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

Loading…