3-(2H-1,2,3-Trizazol-2-yl)aniline

Synthesis

288-36-8

626-01-7

626248-56-4

16279-73-5

3-Iodoaniline (3.70 g, 16.9 mmol), 1,2,3-triazole (3.91 mL, 67.6 mmol), K3PO4 (7.17 g, 33.8 mmol), finely powdered CuI (1.61 g, 8.45 mmol), and ethylenediamine (0.60 mL, 8.45 mmol) were used as raw materials in a mixture of 30 mL dioxane and 15 mL DMSO in a mixed solvent of 30 mL dioxane and 15 mL DMSO for 3 days at reflux. Upon completion of the reaction, the major product 3-(2H-1,2,3-triazol-2-yl)aniline and the minor product 3-(1H-1,2,3-triazol-1-yl)aniline were obtained in a ratio of about 3:1. The reaction mixture was diluted with 400 mL of EtOAc with vigorous stirring and then filtered through diatomaceous earth, and the filtrate was washed twice with brine and subsequently concentrated under reduced pressure. The target product 3-(2H-1,2,3-triazol-2-yl)aniline (1.86 g, 68% yield) was isolated and purified by fast column chromatography.

References