2-CHLORO-N-(2-METHOXYPHENYL)ACETAMIDE

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

Procedure: To ethanol (100 mL) add benzylamine (35 g, 0.33 mol) and 2-chloro-N-(2-methoxyphenyl)acetamide (22 g, 0.11 mol). Stir and heat the reaction at 50° C. Monitor the progress of the reaction by thin-layer chromatography. Upon completion of the reaction remove the precipitate that has formed by suction filtration and discard. Evaporate the filtrate and partition the residue between ethyl acetate and 2N NaOH(aq). Separate the organic layer and dry it over Na2SO4. Remove the drying agent by filtration and remove the solvent in vacuo. Chromatograph the residue on silica gel (400 g) using hexane/EtOAc (3/1) as eluent to obtain the title compound. heat the reaction at 50° C Monitor the progress of the reaction by thin-layer chromatography Upon completion of the reaction remove the precipitate that has formed by suction filtration and discard Evaporate the filtrate partition the residue between ethyl acetate and 2N NaOH(aq) Separate the organic layer dry it over Na2SO4 Remove the drying agent by filtration remove the solvent in vacuo

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

Procedure: To a stirred solution of 28.1 g of 2-chloro-N-(2-methoxyphenyl)acetamide (C.A. 50, 8730i) in 200 ml toluene was added 58.3 g of dibenzylamine and refluxed for 48 hours. After separation of dibenzylamine hydrochloride, the solvent was removed from the reaction mixture. Crystallization of the residue from isopropylether gave 41.9 g colorless crystals of 2-[bis(phenylmethyl)amino]-N-(2-methoxyphenyl)acetamide, mp 92°-94°. refluxed for 48 hours After separation of dibenzylamine hydrochloride the solvent was removed from the reaction mixture Crystallization of the residue from isopropylether

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

Procedure: To a stirred solution of 28.1 g of 2-chloro-N-(2-methoxyphenyl)acetamide (C.A. 50, 8730i) in 200 ml toluene was added 58.3 g of dibenzylamine and refluxed for 48 hours. After separation of dibenzylamine hydrochloride, the solvent was removed from the reaction mixture. Crystallization of the residue from isopropylether gave 41.9 g colorless crystals of 2-[bis(phenylmethyl)amino]-N-(2-methoxyphenyl)acetamide, mp 92°-94°. refluxed for 48 hours After separation of dibenzylamine hydrochloride the solvent was removed from the reaction mixture Crystallization of the residue from isopropylether

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

Procedure: To ethanol (100 mL) add benzylamine (35 g, 0.33 mol) and 2-chloro-N-(2-methoxyphenyl)acetamide (22 g, 0.11 mol). Stir and heat the reaction at 50° C. Monitor the progress of the reaction by thin-layer chromatography. Upon completion of the reaction remove the precipiate that has formed by suction filtration and discard. Evaporate the filtrate and partition the residue between ethyl acetate and 2N NaOH(aq). Separate the organic layer and dry it over Na2SO4. Remove the drying agent by filtration and remove the solvent in vacuo. Chromatograph the residue on silica gel (400 g) using hexane/EtOAc (3/1) as eluent to obtain the title compound. heat the reaction at 50° C Monitor the progress of the reaction by thin-layer chromatography Upon completion of the reaction remove the precipiate that has formed by suction filtration and discard Evaporate the filtrate partition the residue between ethyl acetate and 2N NaOH(aq) Separate the organic layer dry it over Na2SO4 Remove the drying agent by filtration remove the solvent in vacuo

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

Procedure: To ethanol (100 mL) add benzylamine (35 g, 0.33 mol) and 2-chloro-N-(2-methoxyphenyl)acetamide (22 g, 0.11 mol). Stir and heat the reaction at 50° C. Monitor the progress of the reaction by thin-layer chromatography. Upon completion of the reaction remove the precipitate that has formed by suction filtration and discard. Evaporate the filtrate and partition the residue between ethyl acetate and 2N NaOH(aq). Separate the organic layer and dry it over Na2SO4. Remove the drying agent by filtration and remove the solvent in vacuo. Chromatograph the residue on silica gel (400 g) using hexane/EtOAc (3/1) as eluent to obtain the title compound. heat the reaction at 50° C Monitor the progress of the reaction by thin-layer chromatography Upon completion of the reaction remove the precipitate that has formed by suction filtration and discard Evaporate the filtrate partition the residue between ethyl acetate and 2N NaOH(aq) Separate the organic layer dry it over Na2SO4 Remove the drying agent by filtration remove the solvent in vacuo

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

Procedure: To a stirred solution of 28.1 g of 2-chloro-N-(2-methoxyphenyl)acetamide (C.A. 50, 8730i) in 200 ml toluene was added 58.3 g of dibenzylamine and refluxed for 48 hours. After separation of dibenzylamine hydrochloride, the solvent was removed from the reaction mixture. Crystallization of the residue from isopropylether gave 41.9 g colorless crystals of 2-[bis(phenylmethyl)amino]-N-(2-methoxyphenyl)acetamide, mp 92°-94°. refluxed for 48 hours After separation of dibenzylamine hydrochloride the solvent was removed from the reaction mixture Crystallization of the residue from isopropylether