Azobisisobutyronitrile → HCID 17607598, compound

HRID 415686Notes

Reaction equation

HRID 415686 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-3e1947dbb96642589cbf6068c39ea3bf
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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