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

HRID 1283952Notes

Reaction equation

HRID 1283952 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

A mixture of 29.2g 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. temperatureis heated at 110° for 3 hrs under nitrogen
  2. customThe reaction mixture is triturated with 30 ml methanol
  3. filtrationfiltered
  4. customThe filtrate is evaporated off
  5. dissolutionthe residue is dissolved in chloroform
  6. customchromatographed on a column of 750 g of silica gel
  7. washThe fraction which eluted with 5% methanol in chloroform
  8. customis recrystallized from a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-ad8cb015155e40c39c7c179f8277cc73
Source dataset
uspto-grants-1976_08
Patent number
US03976778

Reaction notes

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