Azobisisobutyronitrile → 5-(Bromomethyl)-2,1,3-benzothiadiazole

HRID 1357748Notes

Reaction equation

HRID 1357748 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2=[N:6][S:7][N:8]=[C:4]2[CH:3]=1.[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:10]=[CH:9][C:5]2=[N:6][S:7][N:8]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27812495-methyl-2,1,3-benzothiadiazole

Product 1

HCID 5910045-(Bromomethyl)-2,1,3-benzothiadiazoleYield 63.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Methylbenzo-2,1,3-thiadiazole (5.0 g, 33 mmol), N-bromosuccinimide (5.92g, 33.3 mmol) and catalytic 2,2′-azobisisobutyronitrile were heated at reflux for 16 hours in chloroform (75 mL). The reaction mixture was cooled and the resulting precipitate was filtered off and discarded. The filtrate was′evaporated and recrystallized from ethanol to provide 4.8 g of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting precipitate was filtered off
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a040c9d7aa57420a8211166b2407305f
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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