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

HRID 2234857Notes

Reaction equation

HRID 2234857 reaction equation
[N:1]1[NH:2][C:3](=[O:8])[NH:4][C:5](=[O:7])[CH:6]=1.[Br:9]Br.N>O>[Br:9][C:6]1[C:5](=[O:7])[NH:4][C:3](=[O:8])[NH:2][N:1]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 680371,2,4-Triazine-3,5(2H,4H)-dione

Product 1

HCID 1512406-Bromo-1,2,4-triazine-3,5(2H,4H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2H-[1,2,4]triazin-3,5-dione (50 g, 442 mmol) is placed in the presence of 60 ml of bromine in 800 ml of water at 60° C. for 10 h. The reaction medium is then slowly added to an ammonia solution until pH=5. It is then extracted in ethyl acetate and the organic phases are dried on MgSO4. After filtration and dry concentration, 1a is isolated in the form of a white solid (79.2 g, yield=93%). TLC silica gel 60 F 254 Merck, CH2Cl2:MeOH 90:10, Rf=0.32.

Workup

  1. extractionIt is then extracted in ethyl acetate
  2. customthe organic phases are dried on MgSO4
  3. filtrationAfter filtration
  4. customdry
  5. concentrationconcentration

Sources & evidence

ORD record
ord-bbacedb8625749678ef53f6a6b65ac50
Source dataset
uspto-grants-2010_05
Patent number
US07713971B2

Reaction notes

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