Cyanogen Bromide → HCID 57286927, compound

HRID 1900147Notes

Reaction equation

HRID 1900147 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].[N:19]#[C:20]Br.[OH-].[Na+]>CCO>[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:20]1=[NH:19]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 667591,2-Ethanediamine, N,N'-bis(2-methylphenyl)-

Product 1

HCID 57286927HCID 57286927, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

N,N' Bistolyl ethylene diamine (105.8 mg, 0.44 mmol) was taken up in EtOH (3 mL) to provide a light purple solution. This solution was then placed in a one-necked round-bottom flask (25 mL) equipped with magnetic stirbar and reflux condenser. To this solution, cyanogen bromide (50 mg, 0.47 mmol) in ethanol (2 mL) was added in a single portion. The resultant reaction mixture was stirred for 1 h. It was noted that the solution turned clear. The solution was then brought to reflux and maintained at that temperature for 16 h. The reflux condenser was then removed, allowing the solvent to evaporate. The reaction mixture was then fused at 150° C. for 30 min to provide a brown solid. This solid was immediately taken up in ethanol (4 mL) and placed into a centrifuge tube. To this solution 1N NaOH was added (8 mL) to provide a "whispy" tan precipitate. After several failed attempts to pellet the precipitate, the solution was simply extracted with chloroform (20 mL). The chloroform was concentrated to dryness to provide a clear oil (108.1 mg, 92.6%).

Workup

  1. customto provide a light purple solution
  2. customThis solution was then placed in a one-necked round-bottom flask
  3. custom(25 mL) equipped with magnetic stirbar
  4. temperaturereflux condenser
  5. customThe resultant reaction mixture
  6. temperatureto reflux
  7. temperaturemaintained at that temperature for 16 h
  8. customThe reflux condenser was then removed
  9. customto evaporate
  10. waitThe reaction mixture was then fused at 150° C. for 30 min
  11. customto provide a brown solid
  12. customplaced into a centrifuge tube
  13. customto provide a "whispy" tan precipitate
  14. extractionthe solution was simply extracted with chloroform (20 mL)
  15. concentrationThe chloroform was concentrated to dryness

Sources & evidence

ORD record
ord-12f2ce01fc3944faabe30f1322379a5b
Source dataset
uspto-grants-1996_11
Patent number
US05574070

Reaction notes

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