Azobisisobutyronitrile → HCID 13105775, compound

HRID 1758766Notes

Reaction equation

HRID 1758766 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]2[CH:20]=[N:21][N:22]=[C:11]2[CH2:10][O:9]1.[Br:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:23][C:20]1[N:12]2[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[O:9][CH2:10][C:11]2=[N:22][N:21]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 13105772HCID 13105772, compound

Product 1

HCID 13105775HCID 13105775, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of Compound 9 prepared in Example 4-(1) (1.2 g), N-bromosuccinimide (0.675 g), and α,α'-azobis-isobutyronitrile (10 mg) in carbon tetrachloride (70 ml) is refluxed under heating for 1 hour. The insoluble materials are removed by filtration and the solvent is evaporated. The residue is treated on column chromatography (silica gel/ethyl acetate) to give the title compound (0.54 g), which is recrystallized from ethyl acetate. Yield 36.4%.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 1 hour
  3. customThe insoluble materials are removed by filtration
  4. customthe solvent is evaporated
  5. additionThe residue is treated on column chromatography (silica gel/ethyl acetate)

Sources & evidence

ORD record
ord-59eadfe5153a4404926895652891faaf
Source dataset
uspto-grants-1983_02
Patent number
US04374842

Reaction notes

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