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

HRID 1837066Notes

Reaction equation

HRID 1837066 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.CC(N=NC(C#N)(C)C)(C#N)C>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 62.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Methylbenzo-2,1,3-thiadiazole (5 g, 33.3 mmol) in CHCl3 (75 mL) was treated with N-bromosuccinimide (5.32 g, 33.3 mmol) and a catalytic amount of AIBN and heated at reflux for 16 hours. After cooling to ambient temperature, the resulting precipitate was fitered off and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethanol to provide 4.8 g of the title compound. 1H NMR (300 MHz, CDCl3) δ 4.62 (s, 2H), 7.65 (dd, 1H), 8.0 (m, 2H).

Workup

  1. temperatureat reflux for 16 hours
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-0254ffe7341c4f22ad77b9cb756393b8
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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