Azobisisobutyronitrile → 4-(2-Bromomethyl-phenyl)-[1,2,3]thiadiazole

HRID 397496Notes

Reaction equation

HRID 397496 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[N:9][S:10][CH:11]=1.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl>[Br:13][CH2:12][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[N:9][S:10][CH:11]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 112753384-o-Tolyl-[1,2,3]thiadiazole

Product 1

HCID 218662434-(2-Bromomethyl-phenyl)-[1,2,3]thiadiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4-o-tolyl-[1,2,3]thiadiazole (100 mg, 0.57 mmol), N-bromosuccinimide (100 mg, 0.57 mmol) and 2,2′-azobisisobutyronitrile (9.4 mg, 0.057 mmol) in chloroform (10 ml) was heated at reflux temperature for ˜18 h. Additional chloroform was added and the mixture was washed with water, 5% sodium thiosulfate solution and brine. Drying and solvent evaporation gave 4-(2-bromomethyl-phenyl)-[1,2,3]thiadiazole; 1H NMR (CDCl3, 300 MHz) δ8.87 (s, 1H), 7.67-7.39 (m, 4H), 4.71 (s, 2H). cls Step D: 4-(2-Azidomethyl-phenyl)-[1,2,3]thiadiazole (I-13-4)

Workup

  1. temperatureat reflux temperature for ˜18 h
  2. washthe mixture was washed with water, 5% sodium thiosulfate solution and brine
  3. customDrying
  4. customsolvent evaporation

Sources & evidence

ORD record
ord-b32611d68c8c4698945e7dd44d87d035
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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