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

HRID 639830Notes

Reaction equation

HRID 639830 reaction equation
[C:1]([NH:9][NH2:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:11][N:12]=[C:13]=[S:14].C([O-])(O)=O.[Na+].Cl>CC(O)C.O>[CH3:11][N:12]1[C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[N:9][NH:10][C:13]1=[S:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11112Nicotinic acid, hydrazideHCID 11167Methyl isothiocyanateHCID 516892Sodium Bicarbonate

Product 1

HCID 7575824-methyl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Nicotinohydrazide (10 g, 73 mmol) and methyl isothiocyanate (5.6 g, 76 mmol) were mixed in 2-propanol (150 ml) and heated to 70° C. o.n. The reaction was cooled to r.t. and evaporated to dryness. H2O (180 mL) and NaHCO3 (12.8 g, 152 mmol) were added to the residue and the mixture was refluxed o.n. The reaction mixture was cooled to r.t., acidified with concentrated HCl and the title compound, 13.1 g (93%), was collected by filtration. LC-MS (M++1): 193

Workup

  1. temperatureThe reaction was cooled to r.t.
  2. customevaporated to dryness
  3. temperaturethe mixture was refluxed o.n
  4. temperatureThe reaction mixture was cooled to r.t.
  5. filtrationthe title compound, 13.1 g (93%), was collected by filtration

Sources & evidence

ORD record
ord-6bdeeec6ea7f4e14b5c0781491d9c896
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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