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

HRID 1576838Notes

Reaction equation

HRID 1576838 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 (0.11 mole) of creatinine in 100 ml of dry DMF is added 16.41 g (0.1 mole) of m-nitrophenyl isocyanate (previously recrystallized from benzenepentane). After 9 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 benzenepentane)
  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-3786079403ae4ea2b8b7d2c3f16b1743
Source dataset
uspto-grants-1976_09
Patent number
US03983135

Reaction notes

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