Hydrazine hydrate (1:1) → HCID 178434606, compound

Participants

Reaction Conditions

Reaction Steps

N-[(Dimethylamino)ethylidene]-cinnamamide (2.0 g, 9.0 mmol) was added to a solution of hydrazine hydrate (0.59 mL, 10 mmol) and acetic acid (25 mL). The mixture was heated to 90° C. for 3 h, cooled, and concentrated in vacuo. The resulting material was basified (pH 8) with solid K2CO3, and partitioned between ethyl acetate and water. The organics were dried over Na2SO4 and concentrated in vacuo. The resultant material was purified by flash column chromatography on silica eluting with 1:2 hexane-ethyl acetate to afford 3-methyl-5-[(E)-2-phenylethenyl]-1H-1,2,4-triazole (1.6 g, 96% yield) as a white powder. M.p. 131–134° C. 1H NMR (CDCl3,300 MHz) δ 7.68 (d, J=16 Hz, 0.3H), 7.59 (d, J=16 Hz, 0.7H), 7.49 (m, 2H), 7.32 (m, 3H), 7.05 (d, J=16 Hz, 1H), 6.49 (d, J=16 Hz, 0.4H), 6.21 (br s, 0.3H), 5.88 (br s, 0.3H), 2.53 (s, 3H). MS (EI ionization) 184 (M+−H).

Provenance & Evidence