2-propoxyaniline

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

Procedure: 2-Propoxyaniline (0.5 mole) and sodium carbonate (30 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4,5-dimethyl-1,3-dioxolane (0.55 mole) is slowly added and the reaction mixture is heated at reflux for a period of about 1 hour. After this time the reaction mixture is filtered and additional sodium carbonate (5 grams) is added to the filtrate. The mixture is then distilled under reduced pressure to yield the desired product N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-propoxyaniline. equipped with a mechanical stirrer thermometer and reflux condenser the reaction mixture is heated at reflux for a period of about 1 hour After this time the reaction mixture is filtered additional sodium carbonate (5 grams) is added to the filtrate The mixture is then distilled under reduced pressure

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

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

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (4.2 g) and 2-propoxyaniline (3.5 g) is heated with stirring without a solvent at 120° C. for 1 hour. After cooling, methanol is added to the reaction mixture in order to pulverize the solid, and then the product is collected by filtration and recrystallized from a mixture of DMF and water to give ethyl 1,6-dihydro-2-(2-propoxyanilino)-6-oxo-5-pyrimidinecarboxylate (4.5 g). M.p. 198°-200° C. is heated After cooling the product is collected by filtration recrystallized from a mixture of DMF and water

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron 60 mesh (134.5 g., 2.40 mole), concentrated HCl (37.4 cc), ethanol (630 cc), and water (570 cc) are stirred under nitrogen and the temperature of the mixture is raised to reflux. Then o-propoxynitrobenzene (12.5 g., 0.69 mole), is added at reflux over a period of 5 hrs. and refluxed for 3-4 hrs. Then the mixture is neutralized with concentrated ammonia to a pH of 8-9. The temperature is raised to 30° C., and the reaction mass filtered, 200 cc ether added, the organic layer separated. The product distilled at vapor temperature of 65°-67° C. at 0.05-0.03 mm. yielding 77 g of product (74%). the temperature of the mixture is raised to reflux at reflux over a period of 5 hrs and refluxed for 3-4 hrs the reaction mass filtered 200 cc ether added the organic layer separated The product distilled at vapor temperature of 65°-67° C. at 0.05-0.03 mm

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

Procedure: 2-Propoxyaniline (0.5 mole) and sodium carbonate (30 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4,5-dimethyl-1,3-dioxolane (0.55 mole) is slowly added and the reaction mixture is heated at reflux for a period of about 1 hour. After this time the reaction mixture is filtered and additional sodium carbonate (5 grams) is added to the filtrate. The mixture is then distilled under reduced pressure to yield the desired product N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-propoxyaniline. equipped with a mechanical stirrer thermometer and reflux condenser the reaction mixture is heated at reflux for a period of about 1 hour After this time the reaction mixture is filtered additional sodium carbonate (5 grams) is added to the filtrate The mixture is then distilled under reduced pressure

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

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron 60 mesh (134.5 g., 2.40 mole), concentrated HCl (37.4 cc), ethanol (630 cc), and water (570 cc) are stirred under nitrogen and the temperature of the mixture is raised to reflux. Then o-propoxynitrobenzene (12.5 g., 0.69 mole), is added at reflux over a period of 5 hrs. and refluxed for 3-4 hrs. Then the mixture is neutralized with concentrated ammonia to a pH of 8-9. The temperature is raised to 30° C., and the reaction mass filtered, 200 cc ether added, the organic layer separated. The product distilled at vapor temperature of 65°-67° C. at 0.05-0.03 mm. yielding 77 g of product (74%). the temperature of the mixture is raised to reflux at reflux over a period of 5 hrs and refluxed for 3-4 hrs the reaction mass filtered 200 cc ether added the organic layer separated The product distilled at vapor temperature of 65°-67° C. at 0.05-0.03 mm

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

Procedure: 2-Propoxyaniline (0.5 mole) and sodium carbonate (30 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4,5-dimethyl-1,3-dioxolane (0.55 mole) is slowly added and the reaction mixture is heated at reflux for a period of about 1 hour. After this time the reaction mixture is filtered and additional sodium carbonate (5 grams) is added to the filtrate. The mixture is then distilled under reduced pressure to yield the desired product N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-propoxyaniline. equipped with a mechanical stirrer thermometer and reflux condenser the reaction mixture is heated at reflux for a period of about 1 hour After this time the reaction mixture is filtered additional sodium carbonate (5 grams) is added to the filtrate The mixture is then distilled under reduced pressure

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

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron 60 mesh (134.5 g., 2.40 mole), concentrated HCl (37.4 cc), ethanol (630 cc), and water (570 cc) are stirred under nitrogen and the temperature of the mixture is raised to reflux. Then o-propoxynitrobenzene (12.5 g., 0.69 mole), is added at reflux over a period of 5 hrs. and refluxed for 3-4 hrs. Then the mixture is neutralized with concentrated ammonia to a pH of 8-9. The temperature is raised to 30° C., and the reaction mass filtered, 200 cc ether added, the organic layer separated. The product distilled at vapor temperature of 65°-67° C. at 0.05-0.03 mm. yielding 77 g of product (74%). the temperature of the mixture is raised to reflux at reflux over a period of 5 hrs and refluxed for 3-4 hrs the reaction mass filtered 200 cc ether added the organic layer separated The product distilled at vapor temperature of 65°-67° C. at 0.05-0.03 mm

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (4.2 g) and 2-propoxyaniline (3.5 g) is heated with stirring without a solvent at 120° C. for 1 hour. After cooling, methanol is added to the reaction mixture in order to pulverize the solid, and then the product is collected by filtration and recrystallized from a mixture of DMF and water to give ethyl 1,6-dihydro-2-(2-propoxyanilino)-6-oxo-5-pyrimidinecarboxylate (4.5 g). M.p. 198°-200° C. is heated After cooling the product is collected by filtration recrystallized from a mixture of DMF and water