Azobisisobutyronitrile → HCID 11124410, compound

HRID 368781Notes

Reaction equation

HRID 368781 reaction equation
[S:1]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([O:4][CH2:5][C@H:6]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C@H:7]([CH3:16])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:3])=[O:2].C1C(=O)N([Br:39])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[S:1]([C:25]1[CH:26]=[CH:27][C:28]([CH3:29])=[CH:30][CH:31]=1)([O:4][CH2:5][C@H:6]([O:17][Si:18]([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:19])[CH3:20])[C@H:7]([CH3:16])[CH2:8][CH:9]([Br:39])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 10950646HCID 10950646, compound

Product 1

HCID 11124410HCID 11124410, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a 5 L 3-neck round-bottom flask equipped with a mechanical stirrer, reflux condenser and nitrogen inlet was added CCl4 (1680 mL), tosylate 19 (140 g, 0.30 mol), NBS (65 g, 0.365 mol) and AIBN (16.5 g, 0.10 mol). The mixture was degassed by evacuation under full vacuum with stirring, and backfilling with nitrogen (3×). The reaction mixture was then heated to reflux, whereupon the color became dark brown. After 15 min at vigorous reflux, the reaction mixture became light yellow, and chromatographic analysis indicated the reaction was complete. After cooling to room temperature, the reaction was filtered, and the filtrate was concentrated to dryness. The residue was redissolved in hexanes, filtered again, and concentrated to dryness to afford the title compound (170.3 g) as an amber oil.

Workup

  1. customTo a 5 L 3-neck round-bottom flask equipped with a mechanical stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. customThe mixture was degassed by evacuation under full vacuum
  4. temperatureThe reaction mixture was then heated
  5. temperatureto reflux, whereupon the color
  6. filtrationthe reaction was filtered
  7. concentrationthe filtrate was concentrated to dryness
  8. dissolutionThe residue was redissolved in hexanes
  9. filtrationfiltered again
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0dff68a2b51f49d99d98ce80f6022732
Source dataset
uspto-grants-2000_10
Patent number
US06133457

Reaction notes

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