Azobisisobutyronitrile → HCID 59351659, compound

HRID 1889373Notes

Reaction equation

HRID 1889373 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11](=[O:12])[O:10][N:9]=[C:8]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1.[Br:26]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:8]2[N:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:11](=[O:12])[O:10][N:9]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 59351792HCID 59351792, compound

Product 1

HCID 59351659HCID 59351659, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[(2-methoxyethoxy)methyl]-3-(4′-methylbiphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one (46.6 g), N-bromosuccinimide (26.9 g), α,α′-azobisisobutyronitrile (2.2 g) and carbon tetrachloride (500 mL) was stirred at 80° C. for 6 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as colorless oil (30.5 g, 53%).

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-476b5ca6ca9847fbbeb66c4210d65a01
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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