Water → 3-(3-Chloropropyl)-5,5-dimethyl-2,4-imidazolidinedione

HRID 1245326Notes

Reaction equation

HRID 1245326 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].Br[CH2:11][CH2:12][CH2:13][Cl:14].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Cl:14][CH2:13][CH2:12][CH2:11][N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6491DimethylhydantoinHCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonate

Product 1

HCID 106558253-(3-Chloropropyl)-5,5-dimethyl-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,5-dimethylhydantoin (5.25 g), 1-bromo-3-chloropropane (8.5 mL), and Cs2CO3 (20.78 g) in 40 mL DMF was allowed to react overnight. The reaction was poured into 125 mL H2O, extracted with ether, and the combined extracts dried over MgSO4. The crude extract was filtered, then reduced in vacuo to yield a clear oil. The residue was chromatographed (50% EtOAc in hexanes) to yield 3-(3-chloropropyl)-5,5-dimethylimidazolidinedione as a white solid.

Workup

  1. customto react overnight
  2. extractionextracted with ether
  3. dry with materialthe combined extracts dried over MgSO4
  4. extractionThe crude extract
  5. filtrationwas filtered
  6. customto yield a clear oil
  7. customThe residue was chromatographed (50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a2004397838f4978bd246b99427c8017
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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