N-bromobutanimide → 2-(4-Bromomethyl-phenyl)-5-(3-nitro-phenyl)-[1,3,4]thiadiazole

HRID 651398Notes

Reaction equation

HRID 651398 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)=[N:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1C(=O)N([Br:29])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:11][C:12]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][Br:29])=[CH:19][CH:20]=3)=[N:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 226110572-(3'-Nitrophenyl)-5-(p-tolyl)-1,3,4-thiadiazole

Product 1

HCID 226110592-(4-Bromomethyl-phenyl)-5-(3-nitro-phenyl)-[1,3,4]thiadiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-(3′-nitrophenyl)-5-(p-tolyl)-1,3,4-thiadiazole (0.66 g, 2.22 mmol) in CCl4 (75 ml) is added NBS (0.43 g, 2.44 mmol) and refluxed for 12 hours. The mixture is then concentrated and the residue is taken up in chloroform (50 ml) and washed with saturated NaHCO3 (50 ml) and brine (50 ml). The organic layer is dried over MgSO4 and concentrated to yield 2-(3′-nitrophenyl)-5-(p-bromomethylphenyl)-1,3,4-thiadiazole as a tan solid. (0.69 g, 83%). 1H NMR (CDCl3): δ 4.51 (s, 2H), 7.55 (d, 2H), 7.72 (t, 1H), 8.01 (d, 2H), 8.39 (t, 2H), 8.80 (s, 1H).

Workup

  1. temperaturerefluxed for 12 hours
  2. concentrationThe mixture is then concentrated
  3. washwashed with saturated NaHCO3 (50 ml) and brine (50 ml)
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-338f999760654f1498ea56469020f051
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Reaction notes

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