Cyanogen Bromide → HCID 57286927, compound

HRID 1441174Notes

Reaction equation

HRID 1441174 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 1 N 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-69fb7fe9313f454884d0f988c8537896
Source dataset
uspto-grants-1996_03
Patent number
US05502255

Reaction notes

Loading…