Azobisisobutyronitrile → HCID 60194730, compound

HRID 1748992Notes

Reaction equation

HRID 1748992 reaction equation
BrN1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[C:21]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[NH:35][C@H:34]([C:36]([O:38][CH3:39])=[O:37])[CH2:33][S:32]2)=[CH:27][C:26]=1[O:40][C:41](=[O:43])[CH3:42])(=[O:23])[CH3:22]>C(Cl)(Cl)(Cl)Cl>[C:21]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[S:32][CH:33]=[C:34]([C:36]([O:38][CH3:39])=[O:37])[N:35]=2)=[CH:27][C:26]=1[O:40][C:41](=[O:43])[CH3:42])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 60194725HCID 60194725, compound

Product 1

HCID 60194730HCID 60194730, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a CCl4 (5 mL) solvent, NBS (N-bromosuccinimide) (10.6 mg, 0.06 mmol) and AIBN (2,2′-azobis(2-methylpropionitrile)) (3.0 mg) were added to a solution of Compound 105 (11.2 mg, 0.03 mmol), and the reaction mixture was refluxed for 5 hours. After volatile materials evaporate, the residual was distributed between ethyl acetate and water, and an organic layer was dried, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (4:1) to obtain a solid Compound 103 (3.0 mg, 33%).

Workup

  1. temperaturethe reaction mixture was refluxed for 5 hours
  2. customAfter volatile materials evaporate
  3. customan organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-69443716e73a461e89acbf443693881c
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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