Azobisisobutyronitrile → 5-Methyl-2-(4-(4-bromomethylphenyl)-3-thienyl)-[1,3,4]oxadiazole

HRID 398793Notes

Reaction equation

HRID 398793 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[CH:10][S:9][CH:8]=2)=[N:4][N:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.C([O-])(=O)C.[Na+].C1C(=O)N([Br:43])C(=O)C1>C(O)(=O)C.C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][Br:43])=[CH:14][CH:13]=3)=[CH:10][S:9][CH:8]=2)=[N:4][N:3]=1

Participants

7

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 517045Sodium AcetateHCID 189689025-Methyl-2-(4-(4-methylphenyl)-3-thienyl)-[1,3,4]oxadiazole

Product 1

HCID 189689045-Methyl-2-(4-(4-bromomethylphenyl)-3-thienyl)-[1,3,4]oxadiazoleYield 58.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

5-Methyl-2-(4-(4-methylphenyl)-3-thienyl)-[1,3,4]oxadiazole (3.4 g, 13.3 mmol) was dissolved into carbontetrachloride (60 ml). AIBN (0.21 g), sodium acetate (0.52 g), NBS (2.6 g, 14.6 mmol) and glacial acetic acid (0.52 ml) were added. The reaction mixture was heated at reflux temperature for 8h and then allowed to cool to ambient temperature. The reaction mixture was filtered through silica gel and the filtrate was evaporated in vacuo. The oily residue was dried in vacuo over sodium hydroxide to give 2.6 g of crude 5-methyl-2-(4-(4-bromomethylphenyl)-3-thienyl)- [1,3,4]oxadiazole.

Workup

  1. temperatureThe reaction mixture was heated
  2. filtrationThe reaction mixture was filtered through silica gel
  3. customthe filtrate was evaporated in vacuo
  4. dry with materialThe oily residue was dried in vacuo over sodium hydroxide

Sources & evidence

ORD record
ord-21275eec765d46478b90e9129d156540
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

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