creatinine → 1-(1-Methyl-4-oxo-2-imidazolidinylidene)-3-p-tolyl urea

HRID 2398579Notes

Reaction equation

HRID 2398579 reaction equation
[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.O.[C:10]1([CH3:19])[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[CH:12][CH:11]=1>CN(C=O)C>[CH3:1][N:2]1[CH2:3][C:4](=[O:5])[NH:6][C:7]1=[N:8][C:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([CH3:19])=[CH:11][CH:12]=1)=[O:18]

Participants

5

Reactant 3

HCID 588creatinineHCID 962WaterHCID 693254-Methylphenyl isocyanate

Product 1

HCID 1364097171-(1-Methyl-4-oxo-2-imidazolidinylidene)-3-p-tolyl urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of creatinine (11.88 g, 0.105 mole) in 100 ml dry DMF, p-tolylisocyanate (13.31 g- 0.100 mole) is added dropwise over a period of about 15 minutes with cooling. After stirring for 3.5 hrs., the mixture is poured into about 500 ml iced-water to give white crystals of product which are filtered off and washed with water. Recrystallization of the product from acetone-methanol and then from THF-methanol affords the product, 1-(1-methyl-4-oxo-2-imidazolidinylidene)-3-p-tolyl urea. The crystalline particles are reduced to finer size by adding a solution of the thus-obtained product in minimal DMF to about 1.1 liters of vigorously stirring water, filtering off and drying the resultant fine crystals in vacuo for 24 hours; m.p. 198°-200° C. dec.

Workup

  1. additionis added dropwise over a period of about 15 minutes
  2. temperaturewith cooling
  3. customto give white crystals of product which
  4. filtrationare filtered off
  5. washwashed with water
  6. customRecrystallization of the product from acetone-methanol

Sources & evidence

ORD record
ord-bcc342332ac14e8992ec990091afdb51
Source dataset
uspto-grants-1977_05
Patent number
US04025517

Reaction notes

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