Hydrochloric Acid → 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-amine

Participants

Reaction Conditions

Reaction Steps

2-(4H-[1,2,4]Triazol-3-yl)-isoindole-1,3-dione (1.60 g, 7.48 mmol) was dissolved in DMF (16 ml) and NaH (55% in oil, 500 mg, 11.5 mmol) and SEMCl (2.00 g, 12.0 mmol) was added thereto at room temperature. After stirring at 50° C. for 5 h, the reaction mixture was diluted with EtOAc. The mixture was poured into diluted HCl aq. and the organic layer was washed with brine, dried over MgSO4. The desiccant was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in THF (16 ml) and MeOH (16 ml), and hydrazine hydrate (561 mg, 11.2 mmol) was added thereto. After stirred at room temperature for 15 h, the mixture was concentrated in vacuo. The residue was suspended in EtOAc and the desiccant was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/EtOAc=5/5 to 0/10) to obtain the intended compound as a colorless solid.

Provenance & Evidence