4-cyclopropyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol → 4-(4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridine

HRID 732112Notes

Reaction equation

HRID 732112 reaction equation
[CH:1]1([N:4]2[C:8]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)=[N:7][NH:6][C:5]2=S)[CH2:3][CH2:2]1>[Ni].CCO>[CH:1]1([N:4]2[CH:5]=[N:6][N:7]=[C:8]2[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 49625494-cyclopropyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol

Product 1

HCID 578379644-(4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridineYield 72.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-cyclopropyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione (11.11 g, 51 mmol) was slowly added to wet Raney nickel (90 g ) in EtOH (200 mL) in portions. The reaction mixture was heated at 60° C. for 3.5 h and then filtered through celite. The filtrate was concentrated to give the title compound (6.85 g, 72.3%). 1H-NMR: 8.76 (d, 2H), 8.71 (s, 1H), 7.95 (d, 2H), 3.75(m, 1H), 1.08 (m, 2H) and 0.94 (m, 2H).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-df263967ffd04fac806e74dcc31ef946
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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