creatinine → 57653-26-6

HRID 2398576Notes

Reaction equation

HRID 2398576 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[CH:11]=[C:12]([N:16]=[C:17]=[O:18])[CH:13]=[CH:14][CH:15]=1>CN(C)C=O>[Cl:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]([N:8]=[C:7]2[NH:6][C:4](=[O:5])[CH2:3][N:2]2[CH3:1])=[O:18])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 588creatinineHCID 17968Benzene, 1-chloro-3-isocyanato-

Product 1

HCID 13549769857653-26-6

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of creatinine (5.66 g, 0.05 mole) in 150 ml. of dry dimethylformamide (DMF) is added 7.68 g. (0.05 mole) of m-chlorophenylisocyanate. The mixture is stirred for two hours and heated on a steam bath for 30 minutes. During this time the solution becomes clear (yellow). The solution is filtered and the filtrate cooled. Ice and ice-water are added to the filtrate. A light yellow solid precipitates and is filtered off. After recrystallizations from acetone-methanol and tetrahydrofuran-ether, the pure product, 1-m-chlorophenyl-3-(1-methyl-4-oxo-2-imidazolidinylidene)urea, is obtained, mp 180°-180.5° C.

Workup

  1. temperatureheated on a steam bath for 30 minutes
  2. filtrationThe solution is filtered
  3. temperaturethe filtrate cooled
  4. additionIce and ice-water are added to the filtrate
  5. customA light yellow solid precipitates
  6. filtrationis filtered off
  7. customAfter recrystallizations from acetone-methanol and tetrahydrofuran-ether

Sources & evidence

ORD record
ord-4eb7dfa0bea9410f9fb77e976214d307
Source dataset
uspto-grants-1977_05
Patent number
US04025517

Reaction notes

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