1,4-Dioxane hydrochloride → HCID 66817913, compound

HRID 1754969Notes

Reaction equation

HRID 1754969 reaction equation
Cl.O1CCOCC1.C(O[C:11](=[O:25])[CH2:12][NH:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[C:19]([CH3:24])[CH:18]=1)=[O:15])C>O1CCOCC1>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([N:16]2[C:11](=[O:25])[CH2:12][NH:13][C:14]2=[O:15])=[CH:18][C:19]=1[CH3:24]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 43385039HCID 43385039, compound

Product 1

HCID 66817913HCID 66817913, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4 N HCl-dioxane (7.5 ml, 30 mmol) was added to a solution of the crude product [3-(4-bromo-3-methyl-phenyl)-ureido]-acetic acid ethyl ester (5.07 g) in dioxane (60 ml), and the mixture was heated with stirring at 80° C. for 17 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure, and water was added, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3-(4-bromo-3-methyl-phenyl)-imidazolidine-2,4-dione (2.40 g, 37%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure, and water
  4. additionwas added
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic phase was washed with saturated brine
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5009cb14883842e3a937249bdfc85e6d
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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