Nitrogen → 2-{[2-(methoxymethyl)-1,3-thiazol-4-yl]methyl}-2H-1,2,3-triazol-4-amine

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-(methoxymethyl)-4-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole (200 mg, 0.78 mmol), iron powder (133 mg, 2.35 mmol) and NH4Cl (212 mg, 3.92 mmol) in a mixture of EtOH (10.0 mL) and water (5.0 mL) was stirred at 100° C. for 2 h. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (40 mL) was added followed by 1N NaOH (20 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (2×10 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound which was purified by preparative HPLC to give a colorless oil. LC-MS-conditions 07: tR=0.47 min, [M+H]+=226.30.

Provenance & Evidence