Azobisisobutyronitrile → HCID 54007580, compound

HRID 582459Notes

Reaction equation

HRID 582459 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[S:16]([CH3:19])(=[O:18])=[O:17])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][Br:20])[CH:12]=[CH:11][C:10]=1[S:16]([CH3:19])(=[O:18])=[O:17])(=[O:7])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 54094632HCID 54094632, compound

Product 1

HCID 54007580HCID 54007580, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 46 g (0.152 mol) of N-tert-butyl-2-methanesulfonyl-5-methyl-benzenesulfonamide in 450 ml of CCl4 is, after the addition of 27.0 g (0.152 mol) of NBS (N-bromosuccinimide) and 1 g of AIBN (azobisisobutyronitrile), heated under reflux for 7 h using a daylight lamp. The reaction mixture is then filtered and washed successively with NaHSO3 solution, NaHCO3 solution and water, dried over MgSO4 and completely concentrated in vacuo. 51.2 g of a crude mixture containing 55% by weight of N-tert-butyl-5-bromomethyl-2-methanesulfonylbenzenesulfonamide are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 7 h
  3. filtrationThe reaction mixture is then filtered
  4. washwashed successively with NaHSO3 solution, NaHCO3 solution and water
  5. dry with materialdried over MgSO4
  6. concentrationcompletely concentrated in vacuo
  7. addition51.2 g of a crude mixture containing 55% by weight of N-tert-butyl-5-bromomethyl-2-methanesulfonylbenzenesulfonamide
  8. customare obtained

Sources & evidence

ORD record
ord-c739353e925a491c99ae81b27c5f737b
Source dataset
uspto-grants-1999_07
Patent number
US05925596

Reaction notes

Loading…