Sodium Hydroxide → 4-Ethyl-5-pyridin-4-yl-4h-(1,2,4)triazole-3-thiol

HRID 639779Notes

Reaction equation

HRID 639779 reaction equation
Cl.[C:2](Cl)(=O)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH2:11]([NH:13][C:14](=[S:17])[NH:15][NH2:16])[CH3:12].[OH-].[Na+]>N1C=CC=CC=1>[CH2:11]([N:13]1[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[N:16][NH:15][C:14]1=[S:17])[CH3:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15517804-Ethyl-3-thiosemicarbazideHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 7582734-Ethyl-5-pyridin-4-yl-4h-(1,2,4)triazole-3-thiolYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound (pale yellow solid, 16.7 g, 58%) was prepared from isonicotinoyl chloride hydrochloride (25.1 g, 140.8 mmol) and 4-ethyl-3-thiosemicarbazide (16.87 g, 141.5 mmol) in pyridine (185 ml) with sodium hydroxide (220 mL, 2M, 440 mmol) added to the intermediate formed to effect cyclization. 1H NMR (DMSO-d6) δ (ppm): 8.80 (dd, 2H), 7.72 (dd, 2H), 4.11 (q, 2H), 3.59 (t, 3H).

Workup

  1. additionadded to the intermediate
  2. customformed

Sources & evidence

ORD record
ord-756f7d3cce20469b8df1db71f4afabe3
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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