2-(2-methylpropoxy)aniline

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 solution of 12.5 g of 3.(trifluoromethyl)benzoyl chloride in 60 ml of dichloromethane is added dropwise to a suspension of 9.9 g of 2-(2-methylpropoxy)benzenamine and 33 g of potassium carbonate in 90 ml of dichloromethane, cooled in an ice-bath. cooled in an ice-bath

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

Procedure: A solution of 44 ml of 4-chlorobutyryl chloride in 350 ml of ether is added dropwise to a suspension of 60 g of 2-(2-methylpropoxy)benzenamine and 199 g of potassium carbonate in 500 ml of ether, cooled in an icebath, and the mixture is stirred overnight at room temperature. The mixture is filtered and the filtrate washed successively with 200 ml of 1 N sodium hydroxide, three times 100 ml o& water and 100 ml of saturated sodium chloride solution. The ethereal solution is dried over magnesium sulphate and the solvent evaporated off. 85.8 g of syrupy product are collected, and used without further treatment in the following stage. cooled in an icebath The mixture is filtered the filtrate washed successively with 200 ml of 1 N sodium hydroxide, three times 100 ml o& water and 100 ml of saturated sodium chloride solution The ethereal solution is dried over magnesium sulphate the solvent evaporated off 85.8 g of syrupy product are collected

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 (50 g) and 2-(2-methylpropoxy)aniline (45 g) is heated with stirring at 120° C. for 2 hours. After cooling, ethanol (300 ml) is added to the reaction mixture and the solid is pulverized, 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-(2-methylpropoxy)anilino]-6-oxo-5-pyrimidinecarboxylate (57 g). M.p. 188°-190° C. is heated After cooling the product is collected by filtration recrystallized from a mixture of DMF and water

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 (50 g) and 2-(2-methylpropoxy)aniline (45 g) is heated with stirring at 120° C. for 2 hours. After cooling, ethanol (300 ml) is added to the reaction mixture and the solid is pulverized, 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-(2-methylpropoxy)anilino]-6-oxo-5-pyrimidinecarboxylate (57 g). M.p. 188°-190° C. is heated After cooling the product is collected by filtration recrystallized from a mixture of DMF and water

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

Procedure: 2-(2-Methylpropoxy)-1-nitrobenzene (0.73 g, 75%) was prepared from 2-methyl-propanol (0.46 ml, 5.0 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure G. This was reduced to 2-(2-methylpropoxy)aniline (0.29 g, 70%, 2.5 mmol scale) following general procedure B. N-[2-(2-Methylpropoxy)phenyl]-N′-(thiazol-2-yl)-urea (189 mg, 65%) was prepared from 2-(2-methylpropoxy)aniline (165 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

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

Procedure: 2-(2-Methylpropoxy)-1-nitrobenzene (0.73 g, 75%) was prepared from 2-methyl-propanol (0.46 ml, 5.0 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure G. This was reduced to 2-(2-methylpropoxy)aniline (0.29 g, 70%, 2.5 mmol scale) following general procedure B. N-[2-(2-Methylpropoxy)phenyl]-N′-(thiazol-2-yl)-urea (189 mg, 65%) was prepared from 2-(2-methylpropoxy)aniline (165 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

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

Procedure: A solution of 12.5 g of 3.(trifluoromethyl)benzoyl chloride in 60 ml of dichloromethane is added dropwise to a suspension of 9.9 g of 2-(2-methylpropoxy)benzenamine and 33 g of potassium carbonate in 90 ml of dichloromethane, cooled in an ice-bath. cooled in an ice-bath

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

Procedure: A solution of 44 ml of 4-chlorobutyryl chloride in 350 ml of ether is added dropwise to a suspension of 60 g of 2-(2-methylpropoxy)benzenamine and 199 g of potassium carbonate in 500 ml of ether, cooled in an icebath, and the mixture is stirred overnight at room temperature. The mixture is filtered and the filtrate washed successively with 200 ml of 1 N sodium hydroxide, three times 100 ml o& water and 100 ml of saturated sodium chloride solution. The ethereal solution is dried over magnesium sulphate and the solvent evaporated off. 85.8 g of syrupy product are collected, and used without further treatment in the following stage. cooled in an icebath The mixture is filtered the filtrate washed successively with 200 ml of 1 N sodium hydroxide, three times 100 ml o& water and 100 ml of saturated sodium chloride solution The ethereal solution is dried over magnesium sulphate the solvent evaporated off 85.8 g of syrupy product are collected

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

Procedure: A solution of 44 ml of 4-chlorobutyryl chloride in 350 ml of ether is added dropwise to a suspension of 60 g of 2-(2-methylpropoxy)benzenamine and 199 g of potassium carbonate in 500 ml of ether, cooled in an icebath, and the mixture is stirred overnight at room temperature. The mixture is filtered and the filtrate washed successively with 200 ml of 1 N sodium hydroxide, three times 100 ml o& water and 100 ml of saturated sodium chloride solution. The ethereal solution is dried over magnesium sulphate and the solvent evaporated off. 85.8 g of syrupy product are collected, and used without further treatment in the following stage. cooled in an icebath The mixture is filtered the filtrate washed successively with 200 ml of 1 N sodium hydroxide, three times 100 ml o& water and 100 ml of saturated sodium chloride solution The ethereal solution is dried over magnesium sulphate the solvent evaporated off 85.8 g of syrupy product are collected