Azobisisobutyronitrile → HCID 17607598, compound

HRID 538612Notes

Reaction equation

HRID 538612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13][CH3:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:22][CH:13]([C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:12]=1)[CH3:14]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 28067013-(4-chlorophenyl)-5-ethyl-1,2,4-oxadiazole

Product 1

HCID 17607598HCID 17607598, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(4-Chloro-phenyl)-5-ethyl-[1,2,4]oxadiazole (0.29 g, 1.38 mmol) in CCl4 (10 mL) was added NBS (0.24 g, 1.38 mmol) and AIBN (0.02 g, 0.0001 mmol). The reaction mixture was heated at 100° C. for 2 h under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (230-400 M) using 1% ethyl acetate/hexane as eluent to give the desired product (0.12 g, 30%).

Workup

  1. customAfter the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure
  2. customthe residue was purified by column chromatography on silica (230-400 M)

Sources & evidence

ORD record
ord-e23e3c9b91394bd9b5d0c6bf0a07e562
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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