1,3-Benzodioxol-5-amine, N-ethyl- → N-1,3-Benzodioxol-5-yl-N-ethylurea
Reaction equation
[O:1]([C:3]#[N:4])[Na].[CH2:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1)[CH3:6]>>[CH2:5]([N:7]([C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1)[C:3]([NH2:4])=[O:1])[CH3:6]Participants
3
Procedure
To a solution of N-ethyl-3,4-(methylenedioxy)aniline (8.1 g) AcOH (100 mL) was added NaOCN (3.0 g) at 10° C. he 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).
Workup
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