creatinine → 1-(4-chlorophenyl)-3-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)urea

HRID 1576833Notes

Reaction equation

HRID 1576833 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:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[CH:12][CH:11]=1.O>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]([Cl:9])=[CH:11][CH:12]=1)=[O:18]

Participants

5

Reactant 3

HCID 588creatinineHCID 962WaterHCID 76934-Chlorophenyl Isocyanate

Product 1

HCID 1363546021-(4-chlorophenyl)-3-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)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-chlorophenylisocyanate (15.36 g, 0.100 mole) is added dropwise with cooling. The mixture is stirred for 16 hours and then poured into about 500 ml of iced-water to yield the crystalline product which is filtered off, washed with water and recrystallized twice from acetone-methanol, once from tetrahydrofuran (THF) and then from DMF-methanol. The resultant pure 1-(1-methyl-4-oxo-2-imidazolidinylidene)-3-p-chlorophenylurea is dried in vacuo for 24 hours; m.p. 190°-2°C dec.

Workup

  1. additionis added dropwise
  2. temperaturewith cooling
  3. customto yield the crystalline product which
  4. filtrationis filtered off
  5. washwashed with water
  6. customrecrystallized twice from acetone-methanol, once from tetrahydrofuran (THF)
  7. dry with materialThe resultant pure 1-(1-methyl-4-oxo-2-imidazolidinylidene)-3-p-chlorophenylurea is dried in vacuo for 24 hours

Sources & evidence

ORD record
ord-ce4b1725f0c6407d921b59493edcdf9a
Source dataset
uspto-grants-1976_09
Patent number
US03983135

Reaction notes

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