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

HRID 991507Notes

Reaction equation

HRID 991507 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

Reactant 2

HCID 1183651,3-Benzodioxol-5-amine, N-ethyl-HCID 178418852HCID 178418852, compound

Product 1

HCID 13098802N-1,3-Benzodioxol-5-yl-N-ethylureaYield 59.3%

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

  1. customwas removed
  2. customThe solvent was removed in vacuo
  3. extractionThe mixture was extracted with chloroform (3×50 mL)
  4. washThe combined organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo
  7. customthe resulting residue was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-7df2d677d1b64d85bd7dcaa87bea6a73
Source dataset
uspto-grants-2002_10
Patent number
US06465472B1

Reaction notes

Loading…