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

HRID 1453804Notes

Reaction equation

HRID 1453804 reaction equation
[C:1]([NH:9][NH:10][C:11](=[S:14])[NH:12][CH3:13])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl>O>[CH3:13][N:12]1[C:1]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[N:9][NH:10][C:11]1=[S:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 28240222-isonicotinoyl-N-methylhydrazinecarbothioamide

Product 1

HCID 7385474-methyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiolYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mechanically stirred suspension of 2-isonicotinoyl-N-methylhydrazinecarbothioamide (610 g) in water (5.0 L) was added sodium bicarbonate (390 g) at r.t. The reaction mixture was thereafter slowly heated to 70° C. over 2 h, and maintained at that temperature for another 3.5 h before cooling (ice-bath) to 17° C., followed by adjusting the pH to 3 by slow addition (over 90 min) of concentrated hydrochloric acid (ca. 470 mL). Subsequent filtration of the reaction mixture, followed by washing the collected solid with dilute hydrochloric acid (0.1 N, 2×1.0 L), gave a wet cake that was dried at 100 mbar under a gentle stream of air for 1.5 days to yield 544 g of the title compound.

Workup

  1. temperaturemaintained at that temperature for another 3.5 h
  2. temperaturebefore cooling (ice-bath) to 17° C.
  3. filtrationSubsequent filtration of the reaction mixture
  4. washby washing the collected solid with dilute hydrochloric acid (0.1 N, 2×1.0 L)
  5. customgave a wet cake that
  6. customwas dried at 100 mbar under a gentle stream of air for 1.5 days

Sources & evidence

ORD record
ord-38e52444377f4256b52e58149a25ccd5
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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