Azobisisobutyronitrile → HCID 60194730, compound

HRID 338805Notes

Reaction equation

HRID 338805 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-476ebcbafa3646deb7240afb08dea68c
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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