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

HRID 1884357Notes

Reaction equation

HRID 1884357 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1)[CH3:2].[O:13]([C:15]#[N:16])[Na]>CC(O)=O>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1)[C:15]([NH2:16])=[O:13])[CH3:2]

Participants

4

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%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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%). 1NMR (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. customThe cold bath was 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-1ed9822a53224ceea266fd6bf3261b82
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

Loading…