4-bromo-N-ethylaniline

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

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

Procedure: The reaction procedure of Example 57 was followed except that 1.203 g (7.63 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 639 mg of ammonium thiocyanate, 15 ml of acetone, 1.53 g of N-ethyl-4-bromoaniline and 10 ml of acetone were used. The product was then recrystallized from ethanol to obtain 2.08 g of 2-[N-(4-bromophenyl)-N-ethylamino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one. The reaction procedure of Example 57 The product was then recrystallized from ethanol

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 17.3 g (86.7 mmols) of N-ethyl-4-bromoaniline, 22.7 ml (1.5-fold equivalent weight) of N,N-diisopropylethylamine and 9.64 ml (1.5-fold equivalent weight) of 2-bromoethanol were mixed, and the mixture obtained was heated at 125° C. for 2 hours in an atmosphere of argon. Next, to the reaction solution obtained, 1.5 ml (0.1-fold equivalent weight) of diisopropylethylamine and 0.64 ml (0.1-fold equivalent weight) of 2-bromoethanol were added, and the mixture obtained was heated at 125° C. for 3 hours in an atmosphere of argon. Water was added to the reaction solution obtained, which was then extracted with ethyl acetate. The organic layer obtained was dried with anhydrous magnesium sulfate and then concentrated. The residue thus obtained was purified by silica gel column chromatography developing system (chloroform) to obtain 14.7 g of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline (yield: 69.5%; a colorless oily liquid). the mixture obtained Next, to the reaction solution obtained the mixture obtained was heated at 125° C. for 3 hours in an atmosphere of argon obtained which was then extracted with ethyl acetate The organic layer obtained was dried with anhydrous magnesium sulfate concentrated The residue thus obtained was purified by silica gel column chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 36.8 g (184.1 mmols) of N-ethyl-4-bromoaniline, 48.1 ml (1.5-fold equivalent weight) of N,N-diisopropylethylamine and 28.9 ml (1.2 equivalent) of 6-bromohexanol were mixed, and the mixture obtained was heated at 110° C. for 14 hours in an atmosphere of argon. Water was added to the reaction solution obtained, which was then extracted with ethyl acetate. The organic layer obtained was dried with anhydrous magnesium sulfate and then concentrated. The residue thus obtained was heated under reduced pressure (160° C./0.3 torr), and the components distilled out were removed to obtain 55.6 g of crude N-ethyl-N-(6-hydroxyhexyl)-4-bromoaniline (yield: 100%; a dark-brown oily liquid). the mixture obtained obtained which was then extracted with ethyl acetate The organic layer obtained was dried with anhydrous magnesium sulfate concentrated The residue thus obtained was heated under reduced pressure (160° C./0.3 torr) the components distilled out were removed

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

Procedure: A solution was prepared containing 4.0 g (0.02 mole) of 4-bromo-N-ethylaniline in 25 ml of benzene and one drop each of triethylamine and dibutyltin dilaurate. A solution of 3.7 g (0.02 mole) of benzenesulfonylisocyanate was added to the first solution. The temperature was allowed to rise to 35° C. The mixture was stirred for 2 hours at room temperature and for one-half hour at 40°-45° C. A solution was prepared to rise to 35° C

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

Procedure: The reaction procedure of Example 57 was followed except that 1.203 g (7.63 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 639 mg of ammonium thiocyanate, 15 ml of acetone, 1.53 g of N-ethyl-4-bromoaniline and 10 ml of acetone were used. The product was then recrystallized from ethanol to obtain 2.08 g of 2-[N-(4-bromophenyl)-N-ethylamino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one. The reaction procedure of Example 57 The product was then recrystallized from ethanol

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

Procedure: The reaction procedure of Example 57 was followed except that 1.203 g (7.63 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 639 mg of ammonium thiocyanate, 15 ml of acetone, 1.53 g of N-ethyl-4-bromoaniline and 10 ml of acetone were used. The product was then recrystallized from ethanol to obtain 2.08 g of 2-[N-(4-bromophenyl)-N-ethylamino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one. The reaction procedure of Example 57 The product was then recrystallized from ethanol

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 17.3 g (86.7 mmols) of N-ethyl-4-bromoaniline, 22.7 ml (1.5-fold equivalent weight) of N,N-diisopropylethylamine and 9.64 ml (1.5-fold equivalent weight) of 2-bromoethanol were mixed, and the mixture obtained was heated at 125° C. for 2 hours in an atmosphere of argon. Next, to the reaction solution obtained, 1.5 ml (0.1-fold equivalent weight) of diisopropylethylamine and 0.64 ml (0.1-fold equivalent weight) of 2-bromoethanol were added, and the mixture obtained was heated at 125° C. for 3 hours in an atmosphere of argon. Water was added to the reaction solution obtained, which was then extracted with ethyl acetate. The organic layer obtained was dried with anhydrous magnesium sulfate and then concentrated. The residue thus obtained was purified by silica gel column chromatography developing system (chloroform) to obtain 14.7 g of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline (yield: 69.5%; a colorless oily liquid). the mixture obtained Next, to the reaction solution obtained the mixture obtained was heated at 125° C. for 3 hours in an atmosphere of argon obtained which was then extracted with ethyl acetate The organic layer obtained was dried with anhydrous magnesium sulfate concentrated The residue thus obtained was purified by silica gel column chromatography

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 17.3 g (86.7 mmols) of N-ethyl-4-bromoaniline, 22.7 ml (1.5-fold equivalent weight) of N,N-diisopropylethylamine and 9.64 ml (1.5-fold equivalent weight) of 2-bromoethanol were mixed, and the mixture obtained was heated at 125° C. for 2 hours in an atmosphere of argon. Next, to the reaction solution obtained, 1.5 ml (0.1-fold equivalent weight) of diisopropylethylamine and 0.64 ml (0.1-fold equivalent weight) of 2-bromoethanol were added, and the mixture obtained was heated at 125° C. for 3 hours in an atmosphere of argon. Water was added to the reaction solution obtained, which was then extracted with ethyl acetate. The organic layer obtained was dried with anhydrous magnesium sulfate and then concentrated. The residue thus obtained was purified by silica gel column chromatography developing system (chloroform) to obtain 14.7 g of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline (yield: 69.5%; a colorless oily liquid). the mixture obtained Next, to the reaction solution obtained the mixture obtained was heated at 125° C. for 3 hours in an atmosphere of argon obtained which was then extracted with ethyl acetate The organic layer obtained was dried with anhydrous magnesium sulfate concentrated The residue thus obtained was purified by silica gel column chromatography

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

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

Procedure: To a solution of 4-bromo-N-ethylaniline (17.08 g) in DMF (100 ml) were added at room temperature potassium carbonate (17.1 g), sodium iodide (12.4 g) and 2-bromoethylethyl ether (10.2 ml), and the mixture was stirred at 90° C. for 24 hours. To the mixture were added 2-bromoethylethyl ether (5.0 ml), potassium carbonate (6.22 g) and sodium iodide (6.64 g), and the mixture was stirred for 2 days. To the mixture were added 2-bromoethylethyl ether (10.0 ml), potassium carbonate (17.1 g) and sodium iodide (12.4 g), and the mixture was stirred at 90° C. for 3 days. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:9) to give yellow oil of 4-bromo-N-(2-propoxyethyl)-N-ethylaniline (18.11 g). the mixture was stirred for 2 days the mixture was stirred at 90° C. for 3 days the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried with magnesium sulfate Under reduced pressure, the solvent was evaporated the residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:9)

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

Procedure: To a solution of N-ethylaniline (10.0 g) in DMF (50 ml) was added dropwise at room temperature a solution of N-bromosuccinimide (14.69 g) in DMF (100 ml), and the mixture was stirred at room temperature for 19 hours. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give pale yellow oil of 4-bromo-N-ethylaniline (17.08 g). the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried with magnesium sulfate concentrated under reduced pressure