Hydrochloric Acid → 5-(3,5-Difluoro-phenyl)-4-methyl-2,4-dihydro-[1,2,4]triazole-3-thione

HRID 639833Notes

Reaction equation

HRID 639833 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:5]([NH:7][NH2:8])=O.[CH3:13][N:14]=[C:15]=[S:16].C([O-])(O)=O.[Na+].Cl>CC(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[N:14]([CH3:13])[C:15](=[S:16])[NH:8][N:7]=2)[CH:9]=[C:10]([F:12])[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11167Methyl isothiocyanateHCID 516892Sodium BicarbonateHCID 27369243,5-Difluorobenzohydrazide

Product 1

HCID 703281195-(3,5-Difluoro-phenyl)-4-methyl-2,4-dihydro-[1,2,4]triazole-3-thione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

3,5-difluorobenzohydrazide (5 g, 29 mol) and methyl isothiocyanate (2.1 g, 29 mmol) were mixed in 2-propanol (100 ml) and heated to 70° C. o.n. The reaction was cooled to r.t. and the formed precipitate was filtered off. H2O (100 mL) and NaHCO3 (4 g, 48 mmol) were added to the solid and the mixture was heated to 70° C. for 2 h. The reaction mixture was cooled to r.t., acidified with concentrated HCl and the title compound, 6.4 g (97%), was collected by filtration. LC-MS (M++1): 228

Workup

  1. temperatureThe reaction was cooled to r.t.
  2. filtrationthe formed precipitate was filtered off
  3. temperaturethe mixture was heated to 70° C. for 2 h
  4. temperatureThe reaction mixture was cooled to r.t.
  5. filtrationthe title compound, 6.4 g (97%), was collected by filtration

Sources & evidence

ORD record
ord-4151e314786346a894475e2befb8ecc6
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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