HCID 178418894, compound → 3-(2,4-dimethoxy-phenyl)-4-isobutyl-4H-[1,2,4]triazole

HRID 10734Notes

Reaction equation

HRID 10734 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:12]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:13](S)=[N:14][N:15]=1>C(O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:12]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH:13]=[N:14][N:15]=1

Participants

4

Reactant 1

HCID 178418894HCID 178418894, compound

Product 1

HCID 219810123-(2,4-dimethoxy-phenyl)-4-isobutyl-4H-[1,2,4]triazoleYield 101.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

Ex-109D: To a solution of 5-(2,4-dimethoxy-phenyl)-4-isobutyl-4H-[1,2,4]triazole-3-thiol (Ex-109C, 0.1 g, 0.34 mmol) in ethanol (10 mL) was added wet Raney Ni (0.27 g, 4.6 mmol). The suspension of ethanol was refluxed overnight and then passed through a bed of Hyflo Super Gel and diatomaceous earth. The filtrate was concentrated to afford 3-(2,4-dimethoxy-phenyl)-4-isobutyl-4H-[1,2,4]triazole (0.09 g, 100%) as a white solid: 1H NMR (CDCl3) δ 8.15 (s, 1H), 7.34 (d, J=7.8 Hz, 1H), 6.57 (dd, J=7.8, 2.3 Hz, 1H), 6.51 (d, J=2.3 Hz, 1H), 3.85 (s, 3H), 3.75 (s, 3H), 3.62 (d, J=7.5 Hz, 2H), 1.89–1.80 (m, 1H), 0.76 (d, J=6.6 Hz, 6H).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-422333bb2b134df086396efc34ef8002
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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