Methylamine → 5-(2-Methylaminoethoxy)benzofurazan hydrobromide

Participants

Reaction Steps

To a solution of 5-(2-bromoethoxy)benzofurazan (0.84 g, 3.4 mmol) in ethanol (45 ml), contained within a Fisher-Porter pressure vessel cooled with ice/acetone was added methylamine (45 ml). The vessel was sealed, the bath removed and the solution was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue flushed with ethanol. Recrystallization from ethyl acetate-hexane gave 5-(2-methylaminoethoxy)benzofurazan hydrobromide (0.75 g, 81%); 1H NMR (DMSO) δ2.68 (s, 3H), 3.45 (t, 2H), 4.43 (t, 2H), 7.34 (m, 2H), 8.04 (d, 1H, J=9.6 Hz), 8.76 (bs, 2H).

Provenance & Evidence