N-(diformamidomethyl)formamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 1.4 g. portion of 1,3-diphenyl-2-propanone was mixed with 1.0 g. of tris(formylamino)methane in 20 ml. of dimethylformamide. The reaction mixture was stirred at reflux temperature for 3 hours. The mixture was then cooled to approximately room temperature, and poured into water. The precipitated solids were separated by filtration, and the solids were suspended in chloroform. The chloroform was then filtered, and the solids remaining were washed first with water, and then with chloroform. The yield was about 100 mg. of 3,5-diphenyl-4(1H)-pyridone, m.p. greater than 335° C. at reflux temperature for 3 hours The mixture was then cooled to approximately room temperature The precipitated solids were separated by filtration The chloroform was then filtered the solids remaining were washed first with water

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 1.4 g. portion of 1,3-diphenyl-2-propanone was mixed with 1.0 g. of tris(formylamino)methane in 20 ml. of dimethylformamide. The reaction mixture was stirred at reflux temperature for 3 hours. The mixture was then cooled to approximately room temperature, and poured into water. The precipitated solids were separated by filtration, and the solids were suspended in chloroform. The chloroform was then filtered, and the solids remaining were washed first with water, and then with chloroform. The yield was about 100 mg. of 3,5-diphenyl-4(1H)-pyridone, m.p. greater than 335° C. at reflux temperature for 3 hours The mixture was then cooled to approximately room temperature The precipitated solids were separated by filtration The chloroform was then filtered the solids remaining were washed first with water

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 1.4 g. portion of 1,3-diphenyl-2-propanone was mixed with 1.0 g. of tris(formylamino)methane in 20 ml. of dimethylformamide. The reaction mixture was stirred at reflux temperature for 3 hours. The mixture was then cooled to approximately room temperature, and poured into water. The precipitated solids were separated by filtration, and the solids were suspended in chloroform. The chloroform was then filtered, and the solids remaining were washed first with water, and then with chloroform. The yield was about 100 mg. of 3,5-diphenyl-4(1H)-pyridone, m.p. greater than 335° C. at reflux temperature for 3 hours The mixture was then cooled to approximately room temperature The precipitated solids were separated by filtration The chloroform was then filtered the solids remaining were washed first with water

反応条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 9.0 g (59.9 mmol) of 3-bromoacetophenone, 17.1 g (118 mmol) of N,N′,N″-methylidynetrisformamide, 0.57 g (3.0 mmol) of p-toluenesulfonic acid and 27 g of formamide was stirred at 160° C. for 2 hours. After the reaction mixture was cooled to room temperature, a 5% aqueous solution of caustic soda was added thereto, and the mixture was adjusted to pH 4 with a 5% aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and saturated brine, then dried and concentrated. The resultant solid residue was recrystallized from a mixture ethanol:water=1:2 to obtain 2.49 g of 4-(3-bromophenyl)pyrimidine. After the reaction mixture was cooled to room temperature extracted with ethyl acetate The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and saturated brine dried concentrated The resultant solid residue was recrystallized from a mixture ethanol

反応条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 9.0 g (59.9 mmol) of 3-bromoacetophenone, 17.1 g (118 mmol) of N,N′,N″-methylidynetrisformamide, 0.57 g (3.0 mmol) of p-toluenesulfonic acid and 27 g of formamide was stirred at 160° C. for 2 hours. After the reaction mixture was cooled to room temperature, a 5% aqueous solution of caustic soda was added thereto, and the mixture was adjusted to pH 4 with a 5% aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and saturated brine, then dried and concentrated. The resultant solid residue was recrystallized from a mixture ethanol:water=1:2 to obtain 2.49 g of 4-(3-bromophenyl)pyrimidine. After the reaction mixture was cooled to room temperature extracted with ethyl acetate The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and saturated brine dried concentrated The resultant solid residue was recrystallized from a mixture ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 10.0 g of 2-[4-(4-acetylphenoxy]-butyl]-1H-isoindole-1,3(2H)-dione (Example 42) 10.0 g of tris(formamido)methane, and 20 ml of formamide are combined and the mixture stirred and heated at 160°-165° C. for 8 hours. After dilution with 100 ml of water, the mixture is rendered basic with 10N NaOH, the precipitate collected, washed with water, and air dried. Recrystallization from ethanol gives the pure compound, m.p. 100°-102° C.; yield, 5.0 g. heated at 160°-165° C. for 8 hours the precipitate collected washed with water, and air dried Recrystallization from ethanol gives the pure compound, m.p. 100°-102° C. yield

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 1.4 g. portion of 1,3-diphenyl-2-propanone was mixed with 1.0 g. of tris(formylamino)methane in 20 ml. of dimethylformamide. The reaction mixture was stirred at reflux temperature for 3 hours. The mixture was then cooled to approximately room temperature, and poured into water. The precipitated solids were separated by filtration, and the solids were suspended in chloroform. The chloroform was then filtered, and the solids remaining were washed first with water, and then with chloroform. The yield was about 100 mg. of 3,5-diphenyl-4(1H)-pyridone, m.p. greater than 335° C. at reflux temperature for 3 hours The mixture was then cooled to approximately room temperature The precipitated solids were separated by filtration The chloroform was then filtered the solids remaining were washed first with water