(3E)-1-(3-chlorophenyl)-3-(1-methyl-4-oxoimidazolidin-2-ylidene)urea

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of creatinine (5.66 g, 0.05 mole) in 150 ml. of dry dimethylformamide (DMF) is added 7.68 g. (0.05 mole) of m-chlorophenylisocyanate. The mixture is stirred for two hours and heated on a steam bath for 30 minutes. During this time the solution becomes clear (yellow). The solution is filtered and the filtrate cooled. Ice and ice-water are added to the filtrate. A light yellow solid precipitates and is filtered off. After recrystallizations from acetone-methanol and tetrahydrofuran-ether, the pure product, 1-m-chlorophenyl-3-(1-methyl-4-oxo-2-imidazolidinylidene)urea, is obtained, mp 180°-180.5° C. heated on a steam bath for 30 minutes The solution is filtered the filtrate cooled Ice and ice-water are added to the filtrate A light yellow solid precipitates is filtered off After recrystallizations from acetone-methanol and tetrahydrofuran-ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of creatinine (5.66 g, 0.05 mole) in 150 ml. of dry dimethylformamide (DMF) is added 7.68 g. (0.05 mole) of m-chlorophenylisocyanate. The mixture is stirred for two hours and heated on a steam bath for 30 minutes. During this time the solution becomes clear (yellow). The solution is filtered and the filtrate cooled. Ice and ice-water are added to the filtrate. A light yellow solid precipitates and is filtered off. After recrystallizations from acetone-methanol and tetrahydrofuran-ether, the pure product, 1-m-chlorophenyl-3-(1-methyl-4-oxo-2-imidazolidinylidene)urea, is obtained, mp 180°-180.5° C. heated on a steam bath for 30 minutes The solution is filtered the filtrate cooled Ice and ice-water are added to the filtrate A light yellow solid precipitates is filtered off After recrystallizations from acetone-methanol and tetrahydrofuran-ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of creatinine (5.66 g, 0.05 mole) in 150 ml. of dry dimethylformamide (DMF) is added 7.68 g (0.05 mole) of m-chlorophenylisocyanate. The mixture is stirred for 2 hours and heated on a steam bath for 30 minutes. During this time the solution becomes clear (yellow). The solution is filtered and the filtrate cooled. Ice and ice-water are added to the filtrate. A light yellow solid precipitates and is filtered off. After recrystallizations from acetone-methanol and tetrahydrofuran-ether, the pure product, 1-m-chlorophenyl-3-(1-methyl-4-oxo-2-imidazolidinylidene)urea, is obtained, mp 180°-180.5°C. heated on a steam bath for 30 minutes The solution is filtered the filtrate cooled Ice and ice-water are added to the filtrate A light yellow solid precipitates is filtered off After recrystallizations from acetone-methanol and tetrahydrofuran-ether