creatinine → 1-(1-Methyl-4-oxo-2-imidazolidinylidene)-3-m-nitrophenyl urea

HRID 2398584Notes

Reaction equation

HRID 2398584 reaction equation
[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.[N+:9]([C:12]1[CH:13]=[C:14]([N:18]=[C:19]=[O:20])[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10]>CN(C=O)C>[CH3:1][N:2]1[CH2:3][C:4](=[O:5])[NH:6][C:7]1=[N:8][C:19]([NH:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=1)=[O:20]

Participants

4

Reactant 2

HCID 588creatinineHCID 768353-Nitrophenyl isocyanate

Product 1

HCID 1363546041-(1-Methyl-4-oxo-2-imidazolidinylidene)-3-m-nitrophenyl urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred slurry of 12.45 g (0.11mole) of creatinine in 100 ml of dry DMF is added 16.41 g (0.1 mole) of m-nitrophenyl isocyanate (previously recrystallized from benzene-pentane). After nine hours, ice water is gradually added until crystallization occurres. A large excess of ice water precipitates the product as gummy crystals which then crystallize. The crude product is allowed to air dry for several days. Recrystallization from THF-H2O followed by THF gives pure product, 1-(1-methyl-4-oxo-2-imidazolidinylidene)-3-m-nitrophenyl urea; m.p. 182°-188° C. sl. dec.

Workup

  1. custompreviously recrystallized from benzene-pentane)
  2. additionice water is gradually added until crystallization
  3. customA large excess of ice water precipitates the product as gummy crystals which
  4. customthen crystallize
  5. customto air dry for several days
  6. customRecrystallization from THF-H2O

Sources & evidence

ORD record
ord-e5e60f7a8f8f456fb676840a429e9930
Source dataset
uspto-grants-1977_05
Patent number
US04025517

Reaction notes

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