4-Fluorobenzoyl chloride → 5-(4-Fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

HRID 732088Notes

Reaction equation

HRID 732088 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=O)=[CH:10][CH:9]=1>N1C=CC=CC=1>[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]2[N:2]([CH3:1])[C:3](=[S:6])[NH:4][N:5]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 9751685-(4-Fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-methylthiosemicarbazid (4.24 g, 40.30 mmol) in pyridine (50 ml) was added dropwise 4-fluorobenzoyl chloride (4.9 ml, 40.00 mmol) and the resulting mixture was stirred at r.t. o.n. The pyridine was removed by evaporation and the residue was heated in aq. sat. NaHCO3 at reflux o.n. After cooling to r.t., the product was collected by filtration, washed with water and dried under vacuum to give 3.22 g (38%) which was used in the next step without further purification. 1H NMR: 3.9 (m, 3 H) 6.98 (t, 2 H) 7.92 (m, 2 H).

Workup

  1. customThe pyridine was removed by evaporation
  2. temperaturethe residue was heated in aq. sat. NaHCO3
  3. temperatureat reflux o.n
  4. temperatureAfter cooling to r.t.
  5. filtrationthe product was collected by filtration
  6. washwashed with water
  7. customdried under vacuum
  8. customto give 3.22 g (38%) which
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-3670454e824b4337be88fe2f8b49f06a
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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