HCID 69521177, compound → HCID 69522534, compound

Participants

Reaction Steps

To 1-methyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole and 2-methyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole (6.3 g, 1:1) were added acetic acid (63 ml) and then, reduced iron (18.9 g), and the mixture was stirred for 18 hours at room temperature. The mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate and saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[[(1-methyl-1,2,3,4-tetrazol-5-yl)methyl]sulfanyl]aniline (1.7 g) and 4-[[(2-methyl-1,2,3,4-tetrazol-5-yl)methyl]sulfanyl]aniline (1.6 g).

Provenance & Evidence