ethyl N-(3-chlorophenyl)carbamate

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

Procedure: Ethyl 3-chlorophenylcarbamate (1.0256 g) was dissolved in diglyme (3 ml), and to the solution were added sodium hydride (205.5 mg) and 2-chloro-3,5-dinitrobenzotrifluoride (1.1583 g). The reaction mixture was stirred at room temperature for 4 hours. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (75 g, hexane:ethyl acetate=5:1) and recrystallized from hexane-ethyl acetate to give the title compound (0.7854 g, 42%). the mixture was extracted with ethyl acetate The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution saturated brine, dried over anhydrous magnesium sulfate concentrated in vacuo The resultant residue was purified by silica gel column (75 g, hexane:ethyl acetate=5:1) recrystallized from hexane-ethyl acetate

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

Procedure: Ethyl 3-chlorophenylcarbamate (1.0256 g) was dissolved in diglyme (3 ml), and to the solution were added sodium hydride (205.5 mg) and 2-chloro-3,5-dinitrobenzotrifluoride (1.1583 g). The reaction mixture was stirred at room temperature for 4 hours. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (75 g, hexane:ethyl acetate=5:1) and recrystallized from hexane-ethyl acetate to give the title compound (0.7854 g, 42%). the mixture was extracted with ethyl acetate The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution saturated brine, dried over anhydrous magnesium sulfate concentrated in vacuo The resultant residue was purified by silica gel column (75 g, hexane:ethyl acetate=5:1) recrystallized from hexane-ethyl acetate

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

Procedure: 3-Chloroaniline (2.510 g) was dissolved in pyridine (20 ml), and to the solution was added dropwise ethyl chloroformate (2.257 ml) under ice-cooling. After the mixture was stirred for 1 hour, 1N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (3.9287 g, quantitative yield). cooling the mixture was extracted with ethyl acetate The organic layer was washed with 1N hydrochloric acid saturated brine, dried over anhydrous magnesium sulfate concentrated in vacuo

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

Procedure: 3-Chloroaniline (2.510 g) was dissolved in pyridine (20 ml), and to the solution was added dropwise ethyl chloroformate (2.257 ml) under ice-cooling. After the mixture was stirred for 1 hour, 1N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (3.9287 g, quantitative yield). cooling the mixture was extracted with ethyl acetate The organic layer was washed with 1N hydrochloric acid saturated brine, dried over anhydrous magnesium sulfate concentrated in vacuo

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

Procedure: Ethyl 3-chlorophenylcarbamate (1.0256 g) was dissolved in diglyme (3 ml), and to the solution were added sodium hydride (205.5 mg) and 2-chloro-3,5-dinitrobenzotrifluoride (1.1583 g). The reaction mixture was stirred at room temperature for 4 hours. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (75 g, hexane:ethyl acetate=5:1) and recrystallized from hexane-ethyl acetate to give the title compound (0.7854 g, 42%). the mixture was extracted with ethyl acetate The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution saturated brine, dried over anhydrous magnesium sulfate concentrated in vacuo The resultant residue was purified by silica gel column (75 g, hexane:ethyl acetate=5:1) recrystallized from hexane-ethyl acetate

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

Procedure: 3-Chloroaniline (2.510 g) was dissolved in pyridine (20 ml), and to the solution was added dropwise ethyl chloroformate (2.257 ml) under ice-cooling. After the mixture was stirred for 1 hour, 1N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (3.9287 g, quantitative yield). cooling the mixture was extracted with ethyl acetate The organic layer was washed with 1N hydrochloric acid saturated brine, dried over anhydrous magnesium sulfate concentrated in vacuo