Azobisisobutyronitrile → HCID 68541623, compound

HRID 1446708Notes

Reaction equation

HRID 1446708 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[CH2:9]1[C:14](=O)[N:13](Br)[C:11](=O)[CH2:10]1.CC(N=NC(C#N)(C)C)(C#N)C.C(NCC)C>C(Cl)(Cl)(Cl)Cl>[CH2:11]([N:13]([CH2:14][CH3:9])[CH2:8][C:4]1[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][N:5]=1)[CH3:10]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 8021DiethylamineHCID 67184N-bromobutanimideHCID 126913224-Iodo-2-methylpyridine

Product 1

HCID 68541623HCID 68541623, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

Combine 4-iodo-2-methyl-pyridine (1.1 g, 5 mmol), NBS (0.98 g, 1.1 equiv.) and carbon tetrachloride (50 mL) in a round bottomed flask under nitrogen. Add AIBN (82 mg, 0.1 equiv.) and heat reaction overnight at reflux. Filter the reaction, washing with hexanes. Concentrate filtrate to approximately 10-20 mL volume. Redissolve in THF (20 mL) and cool to 0° C. under nitrogen. Add diethylamine (1.04 mL, 2 equiv.) dropwise via syringe and stir one hour at 0° C. Remove cooling bath and let warm to room temperature. After 6 hours total, concentrate to dryness and purify by silica gel (1:1 Hexanes:Ethyl Acetate→Ethyl Acetate) to give a tan liquid (0.51 g, 35% over 2 steps). MS (ES), m/z 291.0 (M+1).

Workup

  1. customreaction overnight
  2. temperatureat reflux
  3. filtrationFilter
  4. customthe reaction
  5. washwashing with hexanes
  6. dissolutionRedissolve in THF (20 mL)
  7. customRemove
  8. temperaturecooling bath
  9. temperaturelet warm to room temperature
  10. concentrationconcentrate to dryness
  11. custompurify by silica gel (1:1 Hexanes:Ethyl Acetate→Ethyl Acetate)
  12. customto give a tan liquid (0.51 g, 35% over 2 steps)

Sources & evidence

ORD record
ord-ce69ba0adb55448cb7d409c49c272306
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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