2-Chloro-4,6-diphenyl-1,3,5-triazine → HCID 66797708, compound

HRID 2275922Notes

Reaction equation

HRID 2275922 reaction equation
[C:1]1([C:7]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:15]3=[CH:16][C:17]4[NH:18][C:19]5[C:24]([C:25]=4[CH:26]=[C:14]3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:36]1[N:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:39]=[C:38]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[N:37]=1>CN(C)C=O>[C:48]1([C:38]2[N:39]=[C:40]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[N:41]=[C:36]([N:18]3[C:17]4[CH:16]=[C:15]5[C:7]([C:27]6[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=6)([C:1]6[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=6)[C:8]6[C:13]([C:14]5=[CH:26][C:25]=4[C:24]4[C:19]3=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:12][CH:11]=[CH:10][CH:9]=6)[N:37]=2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 24758Sodium hydrideHCID 66797980HCID 66797980, compound

Product 1

HCID 66797708HCID 66797708, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6 g (14.6 mmol) of 12,12-diphenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene are dissolved in 100 ml of dimethylformamide under a protective-gas atmosphere, and 0.76 g of NaH, 60% in mineral oil (19 mmol), is added. After 1 hour at room temperature, a solution of 2-chloro-4,6-diphenyl-1,3,5-triazine (4.3 g, 16 mmol) in 50 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 8.1 g (12.7 mmol, 87%).

Workup

  1. additionis 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-c8e0ff13b04044afa337294cb0f1ad96
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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