2-Imidazolidinone → HCID 57530581, compound

HRID 1454566Notes

Reaction equation

HRID 1454566 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C.C(Cl)Cl>[Si:14]([O:13][CH2:12][CH2:11][CH2:10][N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6])([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 84532-ImidazolidinoneHCID 24758Sodium hydrideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

Product 1

HCID 57530581HCID 57530581, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2-imidazolidone (5.0 g, 60 mmol) in DMF (100 mL) was added NaH (2.4 g, 60% in mineral oil, 60 mmol). The reaction was then heated to 50° C. and was allowed to stir until bubbling of H2 ceased (˜1 hour). To the mixture was added dropwise (3-bromopropoxy)-tert-butyldimethylsilane (13.5 mL, 60 mmol). The reaction mixture was allowed to stir for 3 hours at 50° C. After 3 hours, the reaction was cooled to room temperature and condensed under reduced pressure and then dissolved in DCM (250 mL) and washed with 1N HCl (500 mL), water (500 mL), NaCl (sat.) (500 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was purified via silica gel chromatography (10% MeOH/DCM) to afford the title compound in 45% yield (6.9 g, 26.7 mmol).

Workup

  1. customuntil bubbling of H2
  2. custom(˜1 hour)
  3. stirringto stir for 3 hours at 50° C
  4. temperaturethe reaction was cooled to room temperature
  5. customcondensed under reduced pressure
  6. washwashed with 1N HCl (500 mL), water (500 mL), NaCl (sat.) (500 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customThe crude material was purified via silica gel chromatography (10% MeOH/DCM)

Sources & evidence

ORD record
ord-969f0c84145b4db6ac35a8cc72b53c8a
Source dataset
uspto-grants-2009_01
Patent number
US07479562B2

Reaction notes

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