Cyanuric chloride → 2,4-Dichloro-6-phenyl-1,3,5-triazine

HRID 1586399Notes

Reaction equation

HRID 1586399 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4](Cl)[N:3]=1.[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O1CCCC1>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 178420626HCID 178420626, compound

Product 1

HCID 155492,4-Dichloro-6-phenyl-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 50 g of 2,4,6-trichloro-1,3,5-triazine was added 300 ml of dry tetrahydrofuran and while the mixture was stirred at room temperature, 150 ml of 2M phenylmagnesium bromide-tetrahydrofuran was added dropwise over about 30 minutes. After completion of dropwise addition, the mixture was stirred at room temperature for 1 hour, and then concentrated. To the residue was added iced water and the resultant was extracted with ether. The extract was washed with water, dried over MgSO4, and concentrated. The resulting crystal crop was recrystallized from isopropyl alcohol to provide 21.1 g of 2,4-dichloro-6-phenyl-1,3,5-triazine as pale yellow crystals.

Workup

  1. additionAfter completion of dropwise addition
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. concentrationconcentrated
  4. additionTo the residue was added iced water
  5. extractionthe resultant was extracted with ether
  6. washThe extract was washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe resulting crystal crop was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-321c6c625d8243bc9adf206cc922b7d3
Source dataset
uspto-grants-1999_08
Patent number
US05945426

Reaction notes

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