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

HRID 2275955Notes

Reaction equation

HRID 2275955 reaction equation
[H-].[Na+].Cl[C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=1>CN(C)C=O>[C:10]1([C:8]2[N:9]=[CH:4][N:5]=[C:6]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 24758Sodium hydride

Product 1

HCID 159122,4-diphenyl-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

25 g (62.5 mmol) of product b) are dissolved in 200 ml of dimethylformamide under a protective-gas atmosphere, and 7.7 g of 60% NaH in mineral oil (194 mmol) are added. After 1 h at room temperature, a solution of 2-chloro-4,6-diphenyl-1,3,5-triazine (25 g, 68 mmol) in 300 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 17 g (27 mmol, 44%).

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-9fc419fa673a47d4a1cec402a14e58cd
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

Loading…