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

HRID 639793Notes

Reaction equation

[CH2:1]([N:3]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:6][NH:5][C:4]1=S)[CH3:2]>[Ni].C(O)C>[CH2:1]([N:3]1[CH:4]=[N:5][N:6]=[C:7]1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

4-Ethyl-5-pyridin-4-yl-2,4-dihydro-[1,2,4]triazole-3-thione (4.2 g, 20.4 mmol) was slowly added to Raney nickel (˜40 g, washed three times with 25 mL portions of ethanol) in ethanol (50 mL). The resulting mixture was stirred at 65° C. for approximately 28 hours. The solution mixture was carefully filtered and concentrated in vacuo to yield the title compound (2.88 g, 81.3%). 1H NMR (CDCl3) δ (ppm): 8.81 (d, 2H), 8.33 (s, 1H), 7.62 (d, 2H), 8.18 (q, 2H), 1.51 (t, 3H).

Workup

filtrationThe solution mixture was carefully filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1da05ebcd4c9445eb82ec6a8da2b9eee
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691892B2

Reaction notes

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