2-Imidazolidinone → 1-Ethylsulphonyl-imidazolidin-2-one

HRID 1833589Notes

Reaction equation

HRID 1833589 reaction equation
[CH2:1]1[NH:6][C:4](=[O:5])[NH:3][CH2:2]1.[CH2:7]([S:9](Cl)(=[O:11])=[O:10])[CH3:8]>>[CH2:7]([S:9]([N:3]1[CH2:2][CH2:1][NH:6][C:4]1=[O:5])(=[O:11])=[O:10])[CH3:8]

Participants

3

Reactant 2

HCID 84532-ImidazolidinoneHCID 11667Ethanesulfonyl chloride

Product 1

HCID 112867961-Ethylsulphonyl-imidazolidin-2-one

Procedure

The starting material required is prepared as follows: A mixture of 29.2 g of ethyleneurea and 43.7 g of ethane sulphonyl chloride is heated at 110° for 3 hrs under nitrogen. The reaction mixture is triturated with 30 ml methanol and filtered. The filtrate is evaporated off and the residue is dissolved in chloroform and chromatographed on a column of 750 g of silica gel. The fraction which eluted with 5% methanol in chloroform, is recrystallized from a mixture of methylene chloride and hexane to afford 1-ethylsulphonyl-2-oxo-tetrahydroimidazole which melts at 114°-116°.

Workup

  1. customThe starting material required is prepared
  2. temperatureis heated at 110° for 3 hrs under nitrogen
  3. customThe reaction mixture is triturated with 30 ml methanol
  4. filtrationfiltered
  5. customThe filtrate is evaporated off
  6. dissolutionthe residue is dissolved in chloroform
  7. customchromatographed on a column of 750 g of silica gel
  8. washThe fraction which eluted with 5% methanol in chloroform
  9. customis recrystallized from a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-36acb5f4b4f34ff5830fbdccb1f54133
Source dataset
uspto-grants-1978_01
Patent number
US04066778

Reaction notes

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