benzyl N,N-bis(2-chloroethyl)carbamate

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained. filtered in order to remove the triethylammonium chloride The reaction medium is stirred at ambient temperature for 18 h After the addition of water the reaction medium is extracted with ethyl acetate The organic phase is dried over magnesium sulfate filtered evaporated 20 g of crude residue are obtained purified by chromatography on silica gel, elution

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

実験手順: 13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained. filtered in order to remove the triethylammonium chloride The reaction medium is stirred at ambient temperature for 18 h After the addition of water the reaction medium is extracted with ethyl acetate The organic phase is dried over magnesium sulfate filtered evaporated 20 g of crude residue are obtained purified by chromatography on silica gel, elution

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

実験手順: 13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained. filtered in order to remove the triethylammonium chloride The reaction medium is stirred at ambient temperature for 18 h After the addition of water the reaction medium is extracted with ethyl acetate The organic phase is dried over magnesium sulfate filtered evaporated 20 g of crude residue are obtained purified by chromatography on silica gel, elution

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

実験手順: 13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained. filtered in order to remove the triethylammonium chloride The reaction medium is stirred at ambient temperature for 18 h After the addition of water the reaction medium is extracted with ethyl acetate The organic phase is dried over magnesium sulfate filtered evaporated 20 g of crude residue are obtained purified by chromatography on silica gel, elution

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

実験手順: 13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained. filtered in order to remove the triethylammonium chloride The reaction medium is stirred at ambient temperature for 18 h After the addition of water the reaction medium is extracted with ethyl acetate The organic phase is dried over magnesium sulfate filtered evaporated 20 g of crude residue are obtained purified by chromatography on silica gel, elution

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

実験手順: 13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained. filtered in order to remove the triethylammonium chloride The reaction medium is stirred at ambient temperature for 18 h After the addition of water the reaction medium is extracted with ethyl acetate The organic phase is dried over magnesium sulfate filtered evaporated 20 g of crude residue are obtained purified by chromatography on silica gel, elution

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 0.20 g (1.8 mmol) of 1-(pyrimidin-4-yl)methanamine and 0.61 g (2.2 mmol) benzyl bis(2-chloroethyl)carbamate in 4 mL anhydrous diethylene glycol dimethyl ether was added 3.20 mL (18.3 mmol) of N,N-diisopropylethylamine and 0.05 g (0.40 mmol) of sodium iodide. The resulting solution was heated to 150° C. for 6 h. After cooling to ambient temperature, 12 mL of methanol was added to the mixture followed by 250 mL of diethyl ether. The resulting white precipitate was isolated by vacuum filtration while washing with diethyl ether. Diluted the solid with 100 mL of saturated sodium bicarbonate and extracted the aqueous solution with ethyl acetate (3×100 mL). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound as a white solid which was used without further purification. LC/MS: m/z (ES) 313.1 (MH)+. After cooling to ambient temperature The resulting white precipitate was isolated by vacuum filtration while washing with diethyl ether Diluted the solid with 100 mL of saturated sodium bicarbonate extracted the aqueous solution with ethyl acetate (3×100 mL) The combined organic layers were dried with magnesium sulfate filtered concentrated in vacuo

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 0.20 g (1.8 mmol) of 1-(pyrimidin-4-yl)methanamine and 0.61 g (2.2 mmol) benzyl bis(2-chloroethyl)carbamate in 4 mL anhydrous diethylene glycol dimethyl ether was added 3.20 mL (18.3 mmol) of N,N-diisopropylethylamine and 0.05 g (0.40 mmol) of sodium iodide. The resulting solution was heated to 150° C. for 6 h. After cooling to ambient temperature, 12 mL of methanol was added to the mixture followed by 250 mL of diethyl ether. The resulting white precipitate was isolated by vacuum filtration while washing with diethyl ether. Diluted the solid with 100 mL of saturated sodium bicarbonate and extracted the aqueous solution with ethyl acetate (3×100 mL). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound as a white solid which was used without further purification. LC/MS: m/z (ES) 313.1 (MH)+. After cooling to ambient temperature The resulting white precipitate was isolated by vacuum filtration while washing with diethyl ether Diluted the solid with 100 mL of saturated sodium bicarbonate extracted the aqueous solution with ethyl acetate (3×100 mL) The combined organic layers were dried with magnesium sulfate filtered concentrated in vacuo

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

実験手順: 13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained. filtered in order to remove the triethylammonium chloride The reaction medium is stirred at ambient temperature for 18 h After the addition of water the reaction medium is extracted with ethyl acetate The organic phase is dried over magnesium sulfate filtered evaporated 20 g of crude residue are obtained purified by chromatography on silica gel, elution

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

実験手順: 13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained. filtered in order to remove the triethylammonium chloride The reaction medium is stirred at ambient temperature for 18 h After the addition of water the reaction medium is extracted with ethyl acetate The organic phase is dried over magnesium sulfate filtered evaporated 20 g of crude residue are obtained purified by chromatography on silica gel, elution