Acetic Acid → [3-Bromo-5-(4-nitro-phenylsulphanyl)-phenyl]-ethylmethylamine

Participants

Reaction Steps

0.34 g (0.001 mol) of [3-bromo-5-(4-nitrophenylsulphanyl)-phenyl]-methylamine was dissolved in 10 ml of acetonitrile, treated with 1.4 ml (0.025 mol) of acetaldehyde, 0.74 g (0.010 mol) of NaBH3CN and 1.76 ml of acetic acid and stirred at room temperature for 1 hr. Thereafter, the solvent was removed, the residue was partitioned in ethyl acetate/water and the organic phase was washed with sat. sodium chloride solution, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:19. There was obtained 0.33 g (93%) of [3-bromo-5-(4-nitro-phenylsulphanyl)-phenyl]-ethylmethylamine as an orange-red oil. MS (EI): me/e=368, 366 (C15H15BrN2O2S+).

Provenance & Evidence