2-Imidazolidinone → 1-(N,N-diethylsulphamoyl)-2-oxo-tetrahydroimidazole

HRID 1283954Notes

Reaction equation

HRID 1283954 reaction equation
[CH2:1]1[NH:6][C:4](=[O:5])[NH:3][CH2:2]1.[CH2:7]([N:9]([CH2:14][CH3:15])[S:10](Cl)(=[O:12])=[O:11])[CH3:8]>>[CH2:7]([N:9]([CH2:14][CH3:15])[S:10]([N:3]1[CH2:2][CH2:1][NH:6][C:4]1=[O:5])(=[O:12])=[O:11])[CH3:8]

Participants

3

Reactant 2

HCID 84532-ImidazolidinoneHCID 11252267N,N-diethylsulfamoyl chloride

Product 1

HCID 130317431-(N,N-diethylsulphamoyl)-2-oxo-tetrahydroimidazole

Procedure

A mixture of 5.16 g of ethylene urea and 90 g of N,N-diethyl-sulphamoyl-chloride is heated at 110° for 3 hours. The reaction mixture is cooled and triturated with 300 ml of methanol, filtered and the filtrate evaporated off to dryness and the residue dissolved in 5% methanol in chloroform and chromatographed on a column of silica gel. That fraction which elutes with 5% methanol in chloroform is recrystallized from a mixture of methylenechlorid and hexane to give 1-(N,N-diethylsulphamoyl)--2-oxo-tetrahydroimidazole which melts at 80°-82°.

Workup

  1. temperatureis heated at 110° for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. customtriturated with 300 ml of methanol
  4. filtrationfiltered
  5. customthe filtrate evaporated off to dryness
  6. dissolutionthe residue dissolved in 5% methanol in chloroform
  7. customchromatographed on a column of silica gel
  8. customis recrystallized from a mixture of methylenechlorid and hexane

Sources & evidence

ORD record
ord-c6b434d8d7b146c5ab55a098aa3fda28
Source dataset
uspto-grants-1976_08
Patent number
US03976778

Reaction notes

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