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

HRID 651003Notes

Reaction equation

HRID 651003 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) and 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. washwashed with water (30 ml)
  6. dry with materialThe organic layer is dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-235234aeedf84ebe8a6d780db2f9deb0
Source dataset
uspto-grants-2001_08
Patent number
US06277873B1

Reaction notes

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