2-(5-Oxo-3-thioxo-2,3,4,5-tetrahydro-[1,2,4]triazin-6-ylmethyl)isoindole-1,3-dione → 2-(5-Oxo-4,5-dihydro-[1,2,4]triazin-6-ylmethyl)isoindole-1,3-dione

HRID 2402645Notes

Reaction equation

HRID 2402645 reaction equation
[O:1]=[C:2]1[C:7]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[N:6][NH:5][C:4](=S)[NH:3]1>CCO.[Ni]>[O:1]=[C:2]1[C:7]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[N:6][N:5]=[CH:4][NH:3]1

Participants

4

Reactant 1

HCID 576809502-(5-Oxo-3-thioxo-2,3,4,5-tetrahydro-[1,2,4]triazin-6-ylmethyl)isoindole-1,3-dione

Product 1

HCID 1360179662-(5-Oxo-4,5-dihydro-[1,2,4]triazin-6-ylmethyl)isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A slurry of 2-(5-oxo-3-thioxo-2,3,4,5-tetrahydro-[1,2,4]triazin-6-ylmethyl)isoindole-1,3-dione (1.0 g, 3.47 mmol) in EtOH (40 mL) was charged with excess Raney Ni (3 spatula) and heated to reflux for 2 h. The reaction mixture was filtered hot through a small pad of celite and washed with a hot mixture of EtOH/THF (1:1) (100 mL) and the filtrate was concentrated in vacuo resulting in the title compound as an off-white solid; 1H NMR (DMSO-d6, 400 MHz) δ 4.75 (s, 2H), 7.84-7.98 (m, 4H), 8.66 (s, 1H); MS (ES+): m/z 257.22 (100) [MH+].

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. filtrationThe reaction mixture was filtered hot through a small pad of celite
  4. washwashed with a hot mixture of EtOH/THF (1:1) (100 mL)
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-efc4a165a0a448109978e5770ca3cabb
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

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