2-Chloro-4,6-diphenyl-1,3,5-triazine → HCID 66797777, compound

HRID 2275944Notes

Reaction equation

HRID 2275944 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:10]4[C:14]5[C:19]([S:20][C:9]=4[CH:8]=[CH:7][C:6]=3[C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:18][CH:17]=[CH:16][CH:15]=5.[H-].[Na+].Cl[C:24]1[N:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:27]=[C:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:25]=1>CN(C)C=O>[C:36]1([C:26]2[N:27]=[C:28]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:29]=[C:24]([N:12]3[C:11]4[C:10]5[C:14]6[C:19]([S:20][C:9]=5[CH:8]=[CH:7][C:6]=4[C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:13]3=4)=[CH:18][CH:17]=[CH:16][CH:15]=6)[N:25]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 24758Sodium hydrideHCID 10540204HCID 10540204, compound

Product 1

HCID 66797777HCID 66797777, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

15.1 g (55.4 mmol) of 12H-7-thia-12-azaindeno[1,2-a]fluorene are dissolved in 315 ml of dimethylformamide under a protective-gas atmosphere, and 2.4 g of 60% NaH in mineral oil (61 mmol) are added. After 1 h at room temperature, a solution of 2-chloro-[4,6-bisphenyl]-1,3,5-triazine (17.8 g, 66.5 mmol) in 80 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 recrystallised from toluene. The yield after sublimation is 23.8 g (47.1 mmol, 85%) with a purity of 99.9%.

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. customThe residue is recrystallised from toluene
  7. customThe yield after sublimation

Sources & evidence

ORD record
ord-5d23d788b541417bb86132e914ec8447
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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