Bromine → 6-Bromo-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1513332Notes

Reaction equation

HRID 1513332 reaction equation
[Br:1]Br.[N:3]1[NH:4][C:5](=[O:10])[NH:6][C:7](=[O:9])[CH:8]=1>O>[Br:1][C:8]1[C:7](=[O:9])[NH:6][C:5](=[O:10])[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 680371,2,4-Triazine-3,5(2H,4H)-dione

Product 1

HCID 1512406-Bromo-1,2,4-triazine-3,5(2H,4H)-dioneYield 46.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (2.506 mL, 48.6 mmol) was added to a suspension of 1,2,4-triazine-3,5(2H,4H)-dione (commercially available from Aldrich, 2.5 g, 22.11 mmol) in Water (40 mL). The mixture was stirred at room temperature for 26 hours. A white precipitate was formed. The solid was recovered by filtration and recrystallized from water (15 mL at reflux temperature) affording the title compound 6-bromo-1,2,4-triazine-3,5(2H,4H)-dione (1.97 g, 10.26 mmol, 46.4% yield) as a white crystalline solid.

Workup

  1. customA white precipitate was formed
  2. filtrationThe solid was recovered by filtration
  3. customrecrystallized from water (15 mL at reflux temperature)

Sources & evidence

ORD record
ord-92d153988cc04c6699b8fd7739c1907d
Source dataset
uspto-grants-2012_07
Patent number
US08217168B2

Reaction notes

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