1-Bromo-2-butanone → 2-Amino-1-benzylideneamino-4-ethyl-imidazole

Participants

Reaction Steps

A solution of 1.62 g (0.01 mol) of benzaldehyde guanylhydrazone and 0.84 g (0.005 mol) of 1-bromo-2-butanone (Aldrich, Buchs, Switzerland; tech. 90%, Cat. no. 24,329-9) in 5 ml of ethanol is stirred for one hour in an ice-water bath and for 16 hours at 20° C. The reaction mixture is then concentrated to dryness by evaporation. The residue is taken up in lethyl acetate, washed twice with water and once with dilute sodium chloride solution, and dried over MgSO4. The ethyl acetate solution is concentrated, whereupon the title compound crystallizes out, m.p. 164°-167° C., 1H-NMR (DMSO): δ=8.41 (s, 1H); 8.89 (m, 2H); 7.46 (m, 3H); 7.13 (s, 1H); 5.9 (s, 2H); 2.34 (q, 2H); 1.13 (t, 3H).

Provenance & Evidence