1-methyl-3-phenylurea

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic anhydride (16 ml, 0.17 mole) was added dropwise over three hours to a solution of 1-methyl-3-phenylurea (6 g, 0.04 mole) and malonic acid (4.6 g, 0.04 mole) in acetic acid (40 ml) at 60° C. After the addition was completed, the temperature was raised to 90° C. and maintained for four hours. The solvent was evaporated and the resulting residue treated with 0.1N NaOH (50 ml). After filtration, the solution was acidified with 0.2N HCl (120 ml). The solution was evaporated to dryness under reduced pressure, leaving solid 1-methyl-3-phenyl-2,4,6-(1H,3H,5H)- pyrimidinetrione upon cooling. It was recrystallized from ethanol to yield colorless crystals, m.p. 122.5°-123° C. After the addition maintained for four hours The solvent was evaporated the resulting residue treated with 0.1N NaOH (50 ml) After filtration The solution was evaporated to dryness under reduced pressure

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

Procedure: 1-Methyl-3-phenylurea was prepared by the dropwise addition of methylisocyanate (6 ml, 0.1 mole) over three hours to an ether solution (100 ml) containing aniline (9 ml, 0.1 mole) at 4° C. with stirring. 1-Methyl-3-phenylurea precipitated as purple crystals which were recrystallized from ethanol, m.p. 150° C. 1-Methyl-3-phenylurea precipitated as purple crystals which were recrystallized from ethanol, m.p. 150° C.

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

Procedure: 1-methyl-3-phenyl urea (7.5 g, 0.05 mol) was reacted with 7.5 g (0.05 mol) of chloral without solvent. The mixture was shaken for a short period of time. After, 3 drops of perchloric acid were added and the mixture heated gently for a few minutes to give a homogenous viscous oil. Upon cooling, the product formed as a glass. The chemical analysis showed: %Cl, calculated 35.8, found 35.8; %N, calculated 9.4, found 8.0. The product is the fifth compound tabulated in Table I. the mixture heated gently for a few minutes to give a homogenous viscous oil Upon cooling the product formed as a glass

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

Procedure: 1-methyl-3-phenyl urea (7.5 g, 0.05 mol) was reacted with 7.5 g (0.05 mol) of chloral without solvent. The mixture was shaken for a short period of time. After, three drops of perchloric acid were added and the mixture heated gently for a few minutes to give a homogenous viscous oil. Upon cooling, a glass formed. The chemical analysis showed: %Cl, calculated 35.8, found 35.8; %N, calculated 9.4, found 8.0. the mixture heated gently for a few minutes to give a homogenous viscous oil Upon cooling a glass formed

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

Procedure: 1-methyl-3-phenyl urea (7.5 g, 0.05 mol) was reacted with 7.5 g (0.05 mol) of chloral without solvent. The mixture was shaken for a short period of time. After, three drops of perchloric acid were added and the mixture heated gently for a few minutes to give a homogenous viscous oil. Upon cooling, a glass formed. The chemical analysis showed: %Cl, calculated 35.8, found 35.8; %N, calculated 9.4, found 8.0. the mixture heated gently for a few minutes to give a homogenous viscous oil Upon cooling a glass formed

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

Procedure: To a solution of 38 g (0.44 mol) of cyanacetic acid, 200 ml of acetic anhydride and 200 ml of acetic acid was added 60 g of 1-methyl-3-phenylurea. The solution was stirred at 90°-100° C. for some hours. After cooling, 65.5 g of 1-cyanoaceto-1-methyl-3-phenylurea (XV) was filtered off (mp 180° C). This was dissolved in 3 1 of boiling ethanol and 10 ml of 10% soda solution was added. After cooling and filtration, the filtrate was evaporated and the crystals were washed with ethanol. Yield 46.7 g (XVI) NMR. After cooling 65.5 g of 1-cyanoaceto-1-methyl-3-phenylurea (XV) was filtered off (mp 180° C) This was dissolved in 3 1 of boiling ethanol and 10 ml of 10% soda solution was added After cooling filtration the filtrate was evaporated the crystals were washed with ethanol

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

Procedure: To a solution of 38 g (0.44 mol) of cyanacetic acid, 200 ml of acetic anhydride and 200 ml of acetic acid was added 60 g of 1-methyl-3-phenylurea. The solution was stirred at 90°-100° C. for some hours. After cooling, 65.5 g of 1-cyanoaceto-1-methyl-3-phenylurea (XV) was filtered off (mp 180° C). This was dissolved in 3 1 of boiling ethanol and 10 ml of 10% soda solution was added. After cooling and filtration, the filtrate was evaporated and the crystals were washed with ethanol. Yield 46.7 g (XVI) NMR. After cooling 65.5 g of 1-cyanoaceto-1-methyl-3-phenylurea (XV) was filtered off (mp 180° C) This was dissolved in 3 1 of boiling ethanol and 10 ml of 10% soda solution was added After cooling filtration the filtrate was evaporated the crystals were washed with ethanol

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methyl-N'-phenylurea was preliminarily prepared from phenyl isocyanate and methylamine by the procedure described in Step 1. Using the urea compound as the starting material, uracil ring was formed by the procedure described in Step 2. N-Methyl-N'-phenylurea (30 g, 0.2M) and cyanoacetic acid (18.8 g, 0.22M) were dissolved in 400 ml of a solvent, acetic anhydride, and heated at 80° C. for 2 hours. The solvent acetic anhydride was distilled off under reduced pressure and 200 ml of water was added to the residue, followed by cooling with ice. A 2N aqueous solution of NaOH (220 ml) was then added and the mixture was stirred for 2 hours. A precipitated solid product was obtained by filtration. The solid product was washed successively with water and methanol and dried to yield 6-amino-3-methyl-1-phenyluracil (yield: 33 g, or 76% based on N-methyl-N'-phenylurea). uracil ring was formed by the procedure The solvent acetic anhydride was distilled off under reduced pressure and 200 ml of water was added to the residue by cooling with ice A 2N aqueous solution of NaOH (220 ml) was then added A precipitated solid product was obtained by filtration The solid product was washed successively with water and methanol dried

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methyl-N'-phenylurea was preliminarily prepared from phenyl isocyanate and methylamine by the procedure described in Step 1. Using the urea compound as the starting material, uracil ring was formed by the procedure described in Step 2. N-Methyl-N'-phenylurea (30 g, 0.2M) and cyanoacetic acid (18.8 g, 0.22M) were dissolved in 400 ml of a solvent, acetic anhydride, and heated at 80° C. for 2 hours. The solvent acetic anhydride was distilled off under reduced pressure and 200 ml of water was added to the residue, followed by cooling with ice. A 2N aqueous solution of NaOH (220 ml) was then added and the mixture was stirred for 2 hours. A precipitated solid product was obtained by filtration. The solid product was washed successively with water and methanol and dried to yield 6-amino-3-methyl-1-phenyluracil (yield: 33 g, or 76% based on N-methyl-N'-phenylurea). uracil ring was formed by the procedure The solvent acetic anhydride was distilled off under reduced pressure and 200 ml of water was added to the residue by cooling with ice A 2N aqueous solution of NaOH (220 ml) was then added A precipitated solid product was obtained by filtration The solid product was washed successively with water and methanol dried

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methyl-N'-phenylurea was preliminarily prepared from phenyl isocyanate and methylamine by the procedure described in Step 1. Using the urea compound as the starting material, uracil ring was formed by the procedure described in Step 2. N-Methyl-N'-phenylurea (30 g, 0.2M) and cyanoacetic acid (18.8 g, 0.22M) were dissolved in 400 ml of a solvent, acetic anhydride, and heated at 80° C. for 2 hours. The solvent acetic anhydride was distilled off under reduced pressure and 200 ml of water was added to the residue, followed by cooling with ice. A 2N aqueous solution of NaOH (220 ml) was then added and the mixture was stirred for 2 hours. A precipitated solid product was obtained by filtration. The solid product was washed successively with water and methanol and dried to yield 6-amino-3-methyl-1-phenyluracil (yield: 33 g, or 76% based on N-methyl-N'-phenylurea). uracil ring was formed by the procedure The solvent acetic anhydride was distilled off under reduced pressure and 200 ml of water was added to the residue by cooling with ice A 2N aqueous solution of NaOH (220 ml) was then added A precipitated solid product was obtained by filtration The solid product was washed successively with water and methanol dried