N-bromobutanimide → 5-(4-Fluorophenyl)-3-(p-bromomethylphenyl)-1,2,4-thiadiazole

HRID 1274211Notes

Reaction equation

HRID 1274211 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][Br:27])=[CH:15][CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 226110695-(4'-Fluorophenyl)-3-(p-tolyl)-1,2,4-thiadiazole

Product 1

HCID 226110625-(4-Fluorophenyl)-3-(p-bromomethylphenyl)-1,2,4-thiadiazoleYield 106.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-(4'-fluorophenyl)-3-(p-tolyl)-1,2,4-thiadiazole (0.16 g, 0.59 mmol) in CCl4 (20 ml) is added NBS (0.11 g, 0.59 mmol) and the mixture is heated to reflux for 36 hours. The mixture is cooled to room temperature and filtered through celite. The mother liquor is concentrated. The residue is taken up in chloroform (30 ml) amd washed with water (30 ml). The organic layer is dried over MgSO4 and concentrated to yield 5-(4'-fluorophenyl)-3-(p-bromomethylphenyl)-1,2,4-thiadiazole, (0.22 g) as crude product which is used as is without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 36 hours
  3. filtrationfiltered through celite
  4. concentrationThe mother liquor is concentrated
  5. washamd washed with water (30 ml)
  6. dry with materialThe organic layer is dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-07b0a9e85b2b4c328c9abea84d64fc0c
Source dataset
uspto-grants-2000_12
Patent number
US06156776

Reaction notes

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