Hydrochloric Acid → 4-methyl-5-phenyl-4H-1,2,4-triazole-3-thiol

HRID 1885280Notes

Reaction equation

HRID 1885280 reaction equation
[C:1]([NH:9][NH:10][C:11]([NH:13][CH3:14])=[S:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl>>[CH3:14][N:13]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][NH:10][C:11]1=[S:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 27461131-Benzoyl-4-methyl-3-thiosemicarbazide

Product 1

HCID 7197994-methyl-5-phenyl-4H-1,2,4-triazole-3-thiol

Procedure

A stirred mixture of 1-benzoyl-4-methylthiosemicarbazide (20.9 g, 1.00×10-1 mole) and 1 molar aqueous NaHCO3 (1000 ml, 1 mole) was heated to reflux. After refluxing overnight the reaction was cooled in an ice bath. With stirring the solution was carefully acidified by the dropwise addition of conc. HCl (92 ml, 1.1 mole). A colorless precipitate formed and this was subsequently collected by filtration. Crystallization from ethanol afforded colorless, chunky crystals, Mp 164°-166° C.

Workup

  1. temperaturewas heated to reflux
  2. temperatureAfter refluxing overnight the reaction
  3. temperaturewas cooled in an ice bath
  4. customA colorless precipitate formed
  5. filtrationthis was subsequently collected by filtration
  6. customCrystallization from ethanol afforded colorless

Sources & evidence

ORD record
ord-c89afebb017741d5ad037d7a157e318f
Source dataset
uspto-grants-1992_09
Patent number
US05143933

Reaction notes

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