creatinine → 1-(1-Methyl-4-oxo-2-imidazolidinylidene)-3-p-methoxyphenyl urea
Reaction equation
[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>CN(C=O)C>[CH3:1][N:2]1[CH2:3][C:4](=[O:5])[NH:6][C:7]1=[N:8][C:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring suspension of creatinine (11.88 g, 0.105 mole) in 100 ml dry DMF, p-methoxyphenylisocyanate (14.91 g, 0.100 mole) is added dropwise over a period of about 15 minutes with cooling. After stirring for 8 hours, the mixture is poured into about 500 ml of ice water to yield white crystals of product which are filtered off, washed with water and purified by recrystallization (twice) from tetrahydrofuran-methanol. The crystalline product is reduced to finer size by adding a solution of the product in minimal DMF to vigorously stirred water (about 1.1 liters) and filtering off the resultant crystals which are then dried at room temperature in vacuo for 24 hours; m.p. 193°-5° C. dec.
Workup
- additionis added dropwise over a period of about 15 minutes
- temperaturewith cooling
- customto yield white crystals of product which
- filtrationare filtered off
- washwashed with water
- custompurified by recrystallization (twice) from tetrahydrofuran-methanol
- additionby adding a solution of the product in minimal DMF to vigorously stirred water (about 1.1 liters)
- filtrationfiltering off the resultant crystals which
- customare then dried at room temperature in vacuo for 24 hours
Sources & evidence
- ORD record
- ord-7f841043c3574c7d95eabd0d287280cf
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04025517
Reaction notes
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