Hydrogen Bromide → HCID 18980104, compound

HRID 2392672Notes

Reaction equation

HRID 2392672 reaction equation
[N:1]1([C:6]2[CH:12]=[CH:11][C:9](N)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.N([O-])=O.[Na+].C(N)CN.[BrH:21]>[Cu]Br>[N:1]1([C:6]2[CH:12]=[CH:11][C:9]([Br:21])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 3301EthylenediamineHCID 7358264-(1,2,4-Triazol-1-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 18980104HCID 18980104, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Procedure

4-(1,2,4-Triazol-1-yl)aniline (400 mg, 2.5 mmol) in 48% HBr (10 ml) at -5° C. was stirred while sodium nitrite (173 mg, 2.5 mmol) was added portionwise over 5 minutes. The brown sludge was left stirring for 15 minutes and then added portionwise over 5 minutes to a refluxing mixture of copper (I) bromide (358 mg, 2.5 mmol) in 48% HBr (2 ml). The mixture was then heated at reflux for 1 minute, allowed to cool slightly, and poured into 10% ethylene diamine solution (20 ml). The aqueous solution was extracted with ethyl acetate, dried (Na2SO4), and evaporated to dryness under reduced pressure. The resulting mixture was purified by column chromatography on silica eluting with n-pentane/ethyl acetate (4-10%) to afford the title compound as a white solid (344 mg, 61%).

Workup

  1. additionwas added portionwise over 5 minutes
  2. waitThe brown sludge was left
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for 1 minute
  5. temperatureto cool slightly
  6. extractionThe aqueous solution was extracted with ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. customevaporated to dryness under reduced pressure
  9. customThe resulting mixture was purified by column chromatography on silica eluting with n-pentane/ethyl acetate (4-10%)

Sources & evidence

ORD record
ord-2466ed6eca5040ae81161c88d14b0604
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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