Azobisisobutyronitrile → HCID 57656450, compound

HRID 911609Notes

Reaction equation

HRID 911609 reaction equation
C1C(=O)N([Br:8])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[CH:21]1([CH2:26][C:27]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22]1>C(Cl)(Cl)(Cl)Cl>[Br:8][CH2:35][C:32]1[CH:33]=[CH:34][C:29]([C:27](=[O:28])[CH2:26][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 12176451HCID 12176451, compound

Product 1

HCID 57656450HCID 57656450, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

Add NBS (523 mg, 2.94 mmol) and AIBN (44 mg, 0.267 mmol) to a solution of 2-cyclopentyl-1-p-tolyl-ethanone (540 mg, 2.67 mmol) in carbon tetrachloride (80 mL) and heat overnight at 85° C. Add water and extract the aqueous phase with dichloromethane. Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (98:2, 95:5) to obtain the desired intermediate as an oil (479 mg, 64%).

Workup

  1. extractionAdd water and extract the aqueous phase with dichloromethane
  2. dry with materialDry the organic phase over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (98:2, 95:5)

Sources & evidence

ORD record
ord-8480a64466dd4c97a91ffecf2b8d491c
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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