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

HRID 1023489

반응식

HRID 1023489 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-216fce600ee54f088b0eb9a681441988
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722715B2

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