Hydrogen Bromide → 2-Amino-5-bromo-1H-pyrrole-3,4-dicarbonitrile

HRID 2175723Notes

Reaction equation

HRID 2175723 reaction equation
[C:1]([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#[N:2].[BrH:11]>CC(C)=O.C(OCC)(=O)C.C(O)(=O)C>[NH2:2][C:1]1[NH:6][C:5]([Br:11])=[C:4]([C:7]#[N:8])[C:3]=1[C:9]#[N:10]

Participants

6

Reactant 2

HCID 260Hydrogen BromideHCID 12635Tetracyanoethylene

Product 1

HCID 6109782-Amino-5-bromo-1H-pyrrole-3,4-dicarbonitrileYield 66.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetracyanoethylene (10.02 g, 78.23 mmol) was dissolved in the mixed solvent of acetone (60 mL) and ethyl acetate (120 mL), to which hydrogen bromide (33 wt %, 60 mL) dissolved in acetic acid was added at 0˜5° C. The yellow solid compound observed after one hour-stirring was isolated by filtering. After washing the compound with cold distilled water (100 mL), the mixture was dried in the air to give the target compound (11.02 g, 52.22 mmol, 66.8%).

Workup

  1. additionwas added at 0˜5° C
  2. customwas isolated
  3. filtrationby filtering
  4. washAfter washing the compound
  5. distillationwith cold distilled water (100 mL)
  6. customthe mixture was dried in the air

Sources & evidence

ORD record
ord-d6d498be3d55433a8bde26539f9937fe
Source dataset
uspto-grants-2015_06
Patent number
US09062088B2

Reaction notes

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