Azobisisobutyronitrile → HCID 22731609, compound

HRID 2083850Notes

Reaction equation

HRID 2083850 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:5]2.C1C(=O)N([Br:31])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>>[Br:31][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:5]2

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 15520156-methyl-2,3-diphenylquinoxaline

Product 1

HCID 22731609HCID 22731609, compound

Procedure

6-Methyl-2,3-diphenylquinoxaline (5.0 g, 16.9 mmol) was dissolved in dry, oxygen free benzene (50 ml). The solution was brought to reflux and a mixture of NBS (3.00 g, 16.9 mmol) and AIBN (0.1 g) added as a solid over a period of 30 minutes. The solution was then refluxed for 2 hrs, cooled, washed with water (3×100 ml), dried over MgSO4 and evaporated to leave a pale brown solid. This was recrystallised from hexane/toluene (1:1, 80 ml) to yield 6-bromomethyl-2,3-diphenylquinoxaline, 3.5 g, 56%. Traces of 6-methyl-2,3-diphenylquinoxaline were shown to be present by 1H NMR. A small sample was recrystallised from acetone for characterisation (m.pt. 146-148° C.). Found: C,; H,; N, %; C21H15N2Br requires C, 67.21; H, 4.03; N, 7.47%. 1H NMR (CDCl3, 300 MHz) δ 8.16 (d, J 8.7 Hz, 1H, Hs of quinoxaline), 8.16 (d, J 2.2 Hz, 1H, Hs of quinoxaline), 7.78 (d of d, J 8.7 Hz, J 2.2 Hz, 1H, Hs of quinoxaline), 7.48-7.56 (m, 4H, phenyl ring), 7.30-7.40 (m, 6H, phenyl ring), 4.71 (s, 2H, CH2Br).

Workup

  1. customin dry
  2. temperatureto reflux
  3. additionadded as a solid over a period of 30 minutes
  4. temperatureThe solution was then refluxed for 2 hrs
  5. temperaturecooled
  6. washwashed with water (3×100 ml)
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customto leave a pale brown solid
  10. customThis was recrystallised from hexane/toluene (1:1, 80 ml)

Sources & evidence

ORD record
ord-02c9a548c59241ffbabe9bfffc2a24ba
Source dataset
uspto-grants-2004_04
Patent number
US06716371B1

Reaction notes

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