Azobisisobutyronitrile → HCID 23033213, compound

HRID 1864979Notes

Reaction equation

HRID 1864979 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([N:9]([CH3:10])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21473553HCID 21473553, compound

Product 1

HCID 23033213HCID 23033213, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

The 5, N,N-Trimethyl-2-nitrobenzamide (4.16 g) obtained in Example 9-5b), N-bromosuccinimide (3.56 g) and 2,2′-azobisisobutyronitrile (328 mg) were suspended in carbon tetrachloride (80 mL). The suspension was stirred at 90° C. for 2 hours, filtered through a Celite pad and purified by column chromatography on silica gel with hexane:ethyl acetate=5:4 to give the title compound (602 mg).

Workup

  1. filtrationfiltered through a Celite pad
  2. custompurified by column chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-4ddf199bc1714a058429a247d57c9e6b
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

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