Azobisisobutyronitrile → HCID 19785591, compound

HRID 256604Notes

Reaction equation

HRID 256604 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-38616543f18141c1a008e0fc407257ff
Source dataset
uspto-grants-1993_11
Patent number
US05258399

Reaction notes

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