Hydrochloric Acid → 4-methyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol

HRID 639778Notes

Reaction equation

HRID 639778 reaction equation
Cl.[C:2](Cl)(=O)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:11][NH:12][C:13](=[S:16])[NH:14][NH2:15].[OH-].[Na+].Cl>N1C=CC=CC=1>[CH3:11][N:12]1[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[N:15][NH:14][C:13]1=[S:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723853N-MethylhydrazinecarbothioamideHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 7385474-methyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiolYield 55.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Isonicotinoyl chloride hydrochloride (27.5 g, 154.5 mmol) and 4-methyl-3-thiosemicarbazide (16.4 g, 155.9 mmol) were mixed in pyridine (200 ml) and stirred under argon at ambient temperature overnight. After evaporation to dryness, aqueous sodium hydroxide (250 mL, 2M, 500 mmol) was added and the resulting solution was heated at 60° C. for 16 h. After cooling to room temperature, the solution was neutralized with 6N hydrochloric acid. The precipitate that formed was collected by filtration to give the title compound (pale yellow solid, 16.4 g, 55%). 1H NMR (DMSO-d6), δ (ppm): 8.78 (dd, 2H), 7.75 (dd, 2H), 3.59 (s, 3H).

Workup

  1. additionwas added
  2. temperaturethe resulting solution was heated at 60° C. for 16 h
  3. temperatureAfter cooling to room temperature
  4. customThe precipitate that formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a18ef7d663e54e39b6fc2279194e4e3e
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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