2-imino-1,3-dimethylimidazolidin-4-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 6.35 g (0.050 mole) of 1,3-dimethyl-2-iminoimidazolidin-4-one and 7.25 g (0.050 mole) of 2,6-dimethylphenylisocyanate in 75 ml. of dry tetrahydrofuran is stirred at room temperature for two hours followed by refluxing it for thirty minutes. The reaction mixture is evaporated in vacuo to give a solid, which is crystallized from tetrahydrofuran-ether. Two more recrystallizations from the same solvent mixture gives pure product, 1-(1,3-dimethyl-4-oxo-2-imidazolidinylidene)-3-(2,6-dimethylphenyl) urea; m.p. 115.5°-118.5° C. by refluxing it for thirty minutes The reaction mixture is evaporated in vacuo to give a solid, which is crystallized from tetrahydrofuran-ether Two more recrystallizations from the same solvent mixture

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

Procedure: A mixture of 6.35 g (0.050 mole) of 1,3-dimethyl-2-iminoimidazolidin-4-one, 7.85 g (0.050 mole) of 3-chlorophenylisocyanate and 75 ml of dry tetrahydrofuran is stirred at room temperature for four hours. The solution is evaporated in vacuo and the residue is crystallized from acetonitrile. Two recrystallizations from acetonitrile - ether gives pure product, 1-(3-chlorophenyl)-3-(1,3-dimethyl-4-oxo-2-imidazolidinylidene)urea, m.p. 134°-137° C. The solution is evaporated in vacuo the residue is crystallized from acetonitrile Two recrystallizations from acetonitrile - ether

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

Procedure: A mixture of 6.35 g (0.050 mole) of 1,3-dimethyl-2-iminoimidazolidin-4-one, 7.85 g (0.050 mole) of 3-chlorophenylisocyanate and 75 ml of dry tetrahydrofuran is stirred at room temperature for four hours. The solution is evaporated in vacuo and the residue is crystallized from acetonitrile. Two recrystallizations from acetonitrile - ether gives pure product, 1-(3-chlorophenyl)-3-(1,3-dimethyl-4-oxo-2-imidazolidinylidene)urea, m.p. 134°-137° C. The solution is evaporated in vacuo the residue is crystallized from acetonitrile Two recrystallizations from acetonitrile - ether

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

Procedure: Then, to 150 ml of a methanol solution containing 5.17 g (78.4 mmol) of 85% potassium hydroxide, 20 g (78.4 mmol) of 2-imino-1,3-dimethylimidazolidin-4-one hydroiodide was added, and the mixture was stirred at room temperature for 20 minutes. The solvent was distilled off under reduced pressure. Then, to the residue, 200 ml of chloroform was added, and insoluble matters were filtered off. The filtrate was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 9.0 g of 2-imino-1,3-dimethylimidazolidin-4-one. was added The solvent was distilled off under reduced pressure Then, to the residue, 200 ml of chloroform was added insoluble matters were filtered off The filtrate was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure

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

Procedure: A mixture of 6.35 g (0.050 mole) of 1,3-dimethyl-2-iminoimidazolidin-4-one and 7.25 g (0.050 mole) of 2,6-dimethylphenylisocyanate in 75 ml. of dry tetrahydrofuran is stirred at room temperature for two hours followed by refluxing it for thirty minutes. The reaction mixture is evaporated in vacuo to give a solid, which is crystallized from tetrahydrofuran-ether. Two more recrystallizations from the same solvent mixture gives pure product, 1-(1,3-dimethyl-4-oxo-2-imidazolidinylidene)-3-(2,6-dimethylphenyl) urea; m.p. 115.5°-118.5°C. by refluxing it for thirty minutes The reaction mixture is evaporated in vacuo to give a solid, which is crystallized from tetrahydrofuran-ether Two more recrystallizations from the same solvent mixture

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

Procedure: A mixture of 6.35 g (0.050 mole) of 1,3-dimethyl-2-iminoimidazolidin-4-one, 7.85 g (0.050 mole) of 3-chlorophenylisocyanate and 75 ml of dry tetrahydrofuran is stirred at room temperature for 4 hours. The solution is evaporated in vacuo and the residue is crystallized from acetonitrile. Two recrystallizations from acetonitrile - ether gives pure product, 1-(3-chlorophenyl)-3-(1,3-dimethyl-4-oxo-2-imidazolidinylidene)urea, m.p. 134°-137°C. The solution is evaporated in vacuo the residue is crystallized from acetonitrile Two recrystallizations from acetonitrile - ether

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

Procedure: Then, to 150 ml of a methanol solution containing 5.17 g (78.4 mmol) of 85% potassium hydroxide, 20 g (78.4 mmol) of 2-imino-1,3-dimethylimidazolidin-4-one hydroiodide was added, and the mixture was stirred at room temperature for 20 minutes. The solvent was distilled off under reduced pressure. Then, to the residue, 200 ml of chloroform was added, and insoluble matters were filtered off. The filtrate was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 9.0 g of 2-imino-1,3-dimethylimidazolidin-4-one. was added The solvent was distilled off under reduced pressure Then, to the residue, 200 ml of chloroform was added insoluble matters were filtered off The filtrate was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure