creatinine → 1-(3-Chloro-2,6-dimethylphenyl)-3-(1-methyl-4-oxo-2-imidazolidinylidene) urea

HRID 2398581Notes

Reaction equation

HRID 2398581 reaction equation
[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.[Cl:9][C:10]1[C:11]([CH3:20])=[C:12]([N:17]=[C:18]=[O:19])[C:13]([CH3:16])=[CH:14][CH:15]=1>CN(C=O)C>[Cl:9][C:10]1[C:11]([CH3:20])=[C:12]([NH:17][C:18]([N:8]=[C:7]2[NH:6][C:4](=[O:5])[CH2:3][N:2]2[CH3:1])=[O:19])[C:13]([CH3:16])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 588creatinineHCID 124489541-Chloro-3-isocyanato-2,4-dimethylbenzene

Product 1

HCID 1363546031-(3-Chloro-2,6-dimethylphenyl)-3-(1-methyl-4-oxo-2-imidazolidinylidene) urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of 7.92 g (0.07 mole) of creatinine in 50 ml of dry DMF is added 9.08 g (0.05 mole) of 3-chloro-2,6-dimethylphenyl isocyanate. After stirring for four hours, the reaction mixture is filtered through a diatomaceous earth pad to remove unreacted creatinine. Addition of a large excess of ice water precipitates a gummy semisolid mass which eventually crystallizes. After blowing the product to dry it for about eighteen hours, it is recrystallized from acetone-ether. Finally the product is taken up in dichloromethane and the resulting solution is filtered through diatomaceous earth. Concentration and dilution with ether gives pure product, 1-(3-chloro-2,6-dimethylphenyl)-3-(1-methyl-4-oxo-2-imidazolidinylidene) urea; m.p. 140°-141.5° C.

Workup

  1. filtrationthe reaction mixture is filtered through a diatomaceous earth pad
  2. customto remove unreacted creatinine
  3. additionAddition of a large excess of ice water
  4. customprecipitates a gummy semisolid mass which
  5. customeventually crystallizes
  6. customto dry it for about eighteen hours
  7. customit is recrystallized from acetone-ether
  8. filtrationthe resulting solution is filtered through diatomaceous earth
  9. concentrationConcentration and dilution with ether

Sources & evidence

ORD record
ord-a2926c4ccbe14e12b5f49b54ef1e8381
Source dataset
uspto-grants-1977_05
Patent number
US04025517

Reaction notes

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