3-Bromoaniline → 1-(3-Bromophenyl)-2,4-imidazolidinedione

HRID 471832Notes

Reaction equation

HRID 471832 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[CH2:10][C:11]([N:13]=[C:14]=[O:15])=[O:12].C1CCN2C(=NCCC2)CC1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:10][C:11](=[O:12])[NH:13][C:14]2=[O:15])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 78209Chloroacetyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 671609911-(3-Bromophenyl)-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-bromoaniline (1.0 mL, 9.18 mmol) and chloroacetyl isocyanate (0.780 mL, 9.18 mmol) in dioxane (100 mL) was stirred at room temperature for 2 hr. Dioxane (50 mL) and DBU (3.40 mL, 23.0 mmol) were added and the solution stirred at room temperature for 16 hr. The solution was concentrated in vacuo and the residue taken up in EtOAc and H2O. The mixture was then acidified with 1N HCl, then the aqueous phase extracted with EtOAc. The combined organics were then washed with H2O and brine and dried over Na2SO4. The solution was concentrated in vacuo and the residue recrystallized from EtOAc/hexanes to give 1-(3-bromophenyl)-2,4-imidazolidinedione as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.42 (s, 2H), 7.24-7.30 (m, 2H), 7.50-7.52 (m, 1H), 7.87 (s, 1H), 11.27 (s, 1H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. extractionthe aqueous phase extracted with EtOAc
  3. washThe combined organics were then washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated in vacuo
  6. customthe residue recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-d5a1382a5ec845199b121b1a86a5fb36
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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