2-Imidazolidinone → HCID 13031742, compound

HRID 1283950Notes

Reaction equation

HRID 1283950 reaction equation
[CH2:1]1[NH:6][C:4](=[O:5])[NH:3][CH2:2]1.[CH3:7][N:8]([CH3:13])[S:9](Cl)(=[O:11])=[O:10]>>[CH3:7][N:8]([CH3:13])[S:9]([N:3]1[CH2:2][CH2:1][NH:6][C:4]1=[O:5])(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 84532-ImidazolidinoneHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 13031742HCID 13031742, compound

Procedure

The starting material required for the above reaction is prepared as follows: A mixture of 17.2g of ethylene urea and 28.7 g of N,N-dimethyl sulphamoyl chloride is heated at 110° for 3 hours. The reaction mixture is cooled and triturated with 100 ml methanol. Some solid material separated which is discarded. The filtrate is evaporated off to dryness and the residue is dissolved in 5% methanol in chloroform and chromatographed on a column of 150 g of silica gel. The fraction which eluted with 2% methanol in chloroform is recrystallised from a mixture of methylenechloride and hexane to give 1-(N,N-dimethylsulphamoyl)-2-oxo-tetrahydroimidazole which melts at 129°.

Workup

  1. customThe starting material required for the above reaction
  2. customis prepared
  3. temperatureis heated at 110° for 3 hours
  4. temperatureThe reaction mixture is cooled
  5. customtriturated with 100 ml methanol
  6. customSome solid material separated which
  7. customThe filtrate is evaporated off to dryness
  8. dissolutionthe residue is dissolved in 5% methanol in chloroform
  9. customchromatographed on a column of 150 g of silica gel
  10. washThe fraction which eluted with 2% methanol in chloroform
  11. customis recrystallised from a mixture of methylenechloride and hexane

Sources & evidence

ORD record
ord-236ef6f5f811470cbdb7a20909959025
Source dataset
uspto-grants-1976_08
Patent number
US03976778

Reaction notes

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