Water → HCID 12560083, compound

HRID 1464922Notes

Reaction equation

HRID 1464922 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]=O)=[C:6]([CH:15]=1)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1.O>CC(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[N:7][C:8]3[C:13]([N:16]=2)=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=3)[CH:15]=1

Participants

4

Reactant 2

HCID 962WaterHCID 86662012HCID 86662012, compound

Product 1

HCID 12560083HCID 12560083, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-bromo-N-(4-bromophenyl)-2-nitrosoaniline (13-1) (10 g, 28.1 mmol) in AcOH (300 mL) was heated under reflux for 1.5 hrs. Water (400 mL) was then added and the brown precipitate formed was collected by filtration after washing with water (2×200 mL). The product was purified by silica gel chromatography (SiO2, hexanes/DCM=1/1(v/v)) to afford a brown solid, 2,7-dibromophenazine 13-2 (1.52 g, 16% yield). 1H NMR (CDCl3): δ 8.43 (2H, dd, J 2.2, 0.4 Hz), 8.10 (2H, dd, J 9.2, 0.4 Hz), 7.91 (2H, dd, J 9.2, 2.2 Hz) ppm. LC-MS (ESI): m/z 338.6 [M+H]+.

Workup

  1. temperatureunder reflux for 1.5 hrs
  2. customthe brown precipitate formed
  3. filtrationwas collected by filtration
  4. washafter washing with water (2×200 mL)
  5. customThe product was purified by silica gel chromatography (SiO2, hexanes/DCM=1/1(v/v))

Sources & evidence

ORD record
ord-744c7077731c410d820c719526ec2304
Source dataset
uspto-grants-2015_04
Patent number
US08999967B2

Reaction notes

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