Sulfuric Acid → HCID 19438778, compound

HRID 1733876Notes

Reaction equation

HRID 1733876 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]2[C:16](=[O:19])[NH:17][N:18]=[C:11]2[C:10](=[O:20])[NH:9]3)[CH:5]=[CH:4][N:3]=[CH:2]1.S(=O)(=O)(O)O.[Br:26]Br.[OH-].[Na+]>O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:26][C:15]1[CH:14]=[C:13]2[C:8]([NH:9][C:10](=[O:20])[C:11]3[N:12]2[C:16](=[O:19])[NH:17][N:18]=3)=[CH:7][C:6]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 10221022HCID 10221022, compound

Product 1

HCID 19438778HCID 19438778, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 962WaterSolvent

Procedure

To a solution of 0.94 g (~3.5 mmol) of 7-(1H-Imidazol-1-yl)[1,2,4]triazolo [4,3-a]quinoxaline-1,4(2H,5H)-dione in 7.5 ml concentrated (95-97%) sulfuric acid was added first 1.22 g (~3,9 mmol) silver sulfate and then 0.2 ml (~3.9 mmol) bromine. Stirring was continued at 24° C. for 48 h. The reaction mixture was filtered from silver bromide and then poured into 40 ml ice-water. The precipitate was filtered off to give a crude product. To a solution of the crude product in water was added 4N sodium hydroxide to pH=6 to give the title compound as a precipitate (0.42 g; 35%). M.p.>300° C. (decomp.).

Workup

  1. filtrationThe reaction mixture was filtered from silver bromide
  2. additionpoured into 40 ml ice-water
  3. filtrationThe precipitate was filtered off
  4. customto give a crude product

Sources & evidence

ORD record
ord-3facb0816bac48e69a2420af984da269
Source dataset
uspto-grants-1996_07
Patent number
US05532236

Reaction notes

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