Azobisisobutyronitrile → HCID 19785591, compound

HRID 2254663Notes

Reaction equation

HRID 2254663 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:4])=[O:5])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19785605HCID 19785605, compound

Product 1

HCID 19785591HCID 19785591, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of N-methyl-N-(4-tolyl)methanesulphonamide (0.31 g, 1.54 mmol), N-bromosuccinimide (0.28 g, 1.55 mmol) and 2,2'-azobisisobutyronitrile (20 mg) in carbon tetrachloride (20 ml) was refluxed for 2 hours. The mixture was then cooled to ambient temperature and filtered. The solvent was evaporated and the residue partitioned between ethyl acetate (50 ml) and water (50 ml), washed with brine (50 ml) and dried (MgSO4). The solvent was evaporated yielding N-(4-bromomethylphenyl)-N-methylmethanesulphonamide (0.24 g, 54%) which was used without further purification.

Workup

  1. filtrationfiltered
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ethyl acetate (50 ml) and water (50 ml)
  4. washwashed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-cc1555d60e7b43d5868d36aea75bd33b
Source dataset
uspto-grants-1993_08
Patent number
US05236948

Reaction notes

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