Triethylamine → 8-bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1(2H)-one

HRID 711368Notes

Reaction equation

HRID 711368 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][NH2:13])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:21]=[C:22](Cl)OC(Cl)(Cl)Cl>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]3[N:9]2[C:22](=[O:21])[NH:13][N:12]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 52002657-Bromo-2-hydrazinylquinoxaline

Product 1

HCID 668030988-bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 7-bromo-2-hydrazinylquinoxaline (200 mg, 0.83 mmol) in dichloromethane (5 mL) was added triethylamine (0.175 mL, 1.2 mmol), then the solution of diphosgene (0.055 mL, 0.46 mmol) in dichloromethane was added dropwise at 0° C. with stirring under nitrogen atmosphere. After stirring at r.t. for 5 h, the solvent was removed under vacuum, the residue was washed with water, and dried in vacuo to afford the title product 8-bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1(2H)-one as yellow solid in 82% yield (180 mg). m/z 265 (M+H)+.

Workup

  1. stirringAfter stirring at r.t. for 5 h
  2. customthe solvent was removed under vacuum
  3. washthe residue was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-84a79d67dcf54646bf5417f0a12d5ace
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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