1-Methyl-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine → 1-methyl-N-[3-[3-(N,N-dimethylaminomethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amine

Participants

Reaction Steps

A solution of sodium nitrite (1.74 g) in water (15 ml) was added dropwise to a solution of 1-methyl-N5 -[3-[3-(N,N-dimethylaminomethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine (5 g) in concentrated sulphuric acid (3.68 g) and ethanol (200 ml). The reaction mixture was heated at 65° for 4 h, cooled, treated with saturated brine (100 ml) and extracted with ethyl acetate. Evaporation of the organic extract gave a red oil which was extracted with ether. Distillation of the ether extracts gave the title compound as a pale yellow oil (1.8 g) b.p. 190° (0.04 mm). tlc System A,Rg 0.6.

Provenance & Evidence