Dimethylhydantoin → 3-(2-Chloroethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 1023489

Reaction equation

HRID 1023489 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[OH-].[K+].Br[CH2:13][CH2:14][Cl:15]>CCO>[Cl:15][CH2:14][CH2:13][N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7]

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 78491-Bromo-2-ChloroethaneHCID 14797Potassium Hydroxide

Product 1

HCID 2980853-(2-Chloroethyl)-5,5-dimethylimidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,5-Dimethylhydantoin (5 g, 39 mmol, 1 eq.) was added to a solution of potassium hydroxide (2.18 g, 39 mmol, 1 eq.) in EtOH (100 mL). 1-bromo-2-chloroethane (11.2 g, 78 mmol, 2 eq.) was added in one portion. The resulting mixture was refluxed overnight. Reaction was cooled to room temperature and concentrated in vacuo. Crude residue was re-suspended in ethyl acetate (150 mL), and washed with H2O (100 mL), saturated aqueous sodium bicarbonate (100 mL) then brine (100 mL). Organic layer was dried (Na2SO4) and concentrated in vacuo to yield the crude product, which was directly used in the next step. Yield: 5.4 g (73%). LCMS—[M+H] m/z 191.

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customReaction
  3. concentrationconcentrated in vacuo
  4. washwashed with H2O (100 mL), saturated aqueous sodium bicarbonate (100 mL)
  5. dry with materialOrganic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-216fce600ee54f088b0eb9a681441988
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Linked notes

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