1,3-Benzodioxol-5-amine, N-ethyl- → N-1,3-Benzodioxol-5-yl-N-ethylurea

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Reaction Steps

To a solution of N-ethyl-3,4-(methylenedioxy)aniline (8.1 g) in AcOH (100 mL) was added NaOCN (3.0 g) at 10° C. The cold bath was removed and the mixture was stirred at rt for 24 h. The solvent was removed in vacuo and the resulting residue was neutralized with 2 N NaOH. The mixture was extracted with chloroform (3×50 mL). The combined organic phase was washed with water and brine, dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was recrystallized from chloroform/hexane to yield the title compound (5.7 g, 56%). 1H NMR (CDCl3): 6.78-6.72 (m, 3H), 6.02 (s, 2H), 4.38 (br s, 2H), 3.66 (q, J=7.0, 2H), 1.11 (t, J=7.0, 3H).

Provenance & Evidence