Ethyl 2-amino-3,5-dichlorobenzoate

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

Procedure: 138.0 g of 4-chlorobenzenesulfonic acid chloride are added in portions, at room temperature, to a solution of 50.0 g of 3,5-dichloroanthranilic acid ethyl ester in 210 ml of dry pyridine. The reaction mixture is heated to 80°-90° C. and stirred for 28 hours at that temperature to complete the reaction. After cooling, the reaction mixture is poured onto ice/water and acidified with 2N hydrochloric acid. The sticky, oily precipitate is dissolved in diethyl ether, and the aqueous phase is removed. The organic phase is washed with water and saturated sodium chloride solution. After drying over magnesium sulfate, the ether is evaporated off and the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1. The crystals, which are filtered off, weigh 87.3 g after drying and correspond to the title compound (m.p. 148°-150° C.). The reaction mixture is heated to 80°-90° C. the reaction After cooling the reaction mixture is poured onto ice/water the aqueous phase is removed The organic phase is washed with water and saturated sodium chloride solution After drying over magnesium sulfate the ether is evaporated off the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1 The crystals, which are filtered off after drying

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

Procedure: 138.0 g of 4-chlorobenzenesulfonic acid chloride are added in portions, at room temperature, to a solution of 50.0 g of 3,5-dichloroanthranilic acid ethyl ester in 210 ml of dry pyridine. The reaction mixture is heated to 80°-90° C. and stirred for 28 hours at that temperature to complete the reaction. After cooling, the reaction mixture is poured onto ice/water and acidified with 2N hydrochloric acid. The sticky, oily precipitate is dissolved in diethyl ether, and the aqueous phase is removed. The organic phase is washed with water and saturated sodium chloride solution. After drying over magnesium sulfate, the ether is evaporated off and the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1. The crystals, which are filtered off, weigh 87.3 g after drying and correspond to the title compound (m.p. 148°-150° C.). The reaction mixture is heated to 80°-90° C. the reaction After cooling the reaction mixture is poured onto ice/water the aqueous phase is removed The organic phase is washed with water and saturated sodium chloride solution After drying over magnesium sulfate the ether is evaporated off the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1 The crystals, which are filtered off after drying

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

Procedure: To a stirred mixture of 25 parts of ethyl 2-amino-3,5-dichlorobenzoate and 180 parts of dimethylbenzene are added dropwise 30 parts of ethyl carbonochloridate. Upon completion, stirring is continued for 8 hours at reflux temperature. The reaction mixture is evaporated and the residue is crystallized from petroleumether. The product is filtered off and dried, yielding 30 parts of ethyl 3,5-dichloro-2-(ethoxycarbonylamino)benzoate. at reflux temperature The reaction mixture is evaporated the residue is crystallized from petroleumether The product is filtered off dried

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

Procedure: A mixture of 50 parts of 2-amino-3,5-dichlorobenzoic acid and 240 parts of ethanol is saturated with gaseous hydrogen chloride. The whole is stirred and refluxed for 10 hours. The reaction mixture is allowed to cool and the solvent is evaporated. To the solid residue are added water and sodium hydroxide. The precipitated product is filtered off and dried, yielding 25 parts of ethyl 2-amino-3,5-dichlorobenzoate. refluxed for 10 hours to cool the solvent is evaporated To the solid residue are added water and sodium hydroxide The precipitated product is filtered off dried

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

Procedure: To a stirred mixture of 25 parts of ethyl 2-amino-3,5-dichlorobenzoate and 180 parts of dimethylbenzene are added dropwise 30 parts of ethyl carbonochloridate. Upon completion, stirring is continued for 8 hours at reflux temperature. The reaction mixture is evaporated and the residue is crystallized from petroleumether. The product is filtered off and dried, yielding 30 parts of ethyl 3,5-dichloro-2-(ethoxycarbonylamino)benzoate. at reflux temperature The reaction mixture is evaporated the residue is crystallized from petroleumether The product is filtered off dried

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

Procedure: A mixture of 50 parts of 2-amino-3,5-dichlorobenzoic acid and 240 parts of ethanol is saturated with gaseous hydrogen chloride. The whole is stirred and refluxed for 10 hours. The reaction mixture is allowed to cool and the solvent is evaporated. To the solid residue are added water and sodium hydroxide. The precipitated product is filtered off and dried, yielding 25 parts of ethyl 2-amino-3,5-dichlorobenzoate. refluxed for 10 hours to cool the solvent is evaporated To the solid residue are added water and sodium hydroxide The precipitated product is filtered off dried

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

Procedure: 138.0 g of 4-chlorobenzenesulfonic acid chloride are added in portions, at room temperature, to a solution of 50.0 g of 3,5-dichloroanthranilic acid ethyl ester in 210 ml of dry pyridine. The reaction mixture is heated to 80°-90° C. and stirred for 28 hours at that temperature to complete the reaction. After cooling, the reaction mixture is poured onto ice/water and acidified with 2N hydrochloric acid. The sticky, oily precipitate is dissolved in diethyl ether, and the aqueous phase is removed. The organic phase is washed with water and saturated sodium chloride solution. After drying over magnesium sulfate, the ether is evaporated off and the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1. The crystals, which are filtered off, weigh 87.3 g after drying and correspond to the title compound (m.p. 148°-150° C.). The reaction mixture is heated to 80°-90° C. the reaction After cooling the reaction mixture is poured onto ice/water the aqueous phase is removed The organic phase is washed with water and saturated sodium chloride solution After drying over magnesium sulfate the ether is evaporated off the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1 The crystals, which are filtered off after drying

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

Procedure: 138.0 g of 4-chlorobenzenesulfonic acid chloride are added in portions, at room temperature, to a solution of 50.0 g of 3,5-dichloroanthranilic acid ethyl ester in 210 ml of dry pyridine. The reaction mixture is heated to 80°-90° C. and stirred for 28 hours at that temperature to complete the reaction. After cooling, the reaction mixture is poured onto ice/water and acidified with 2N hydrochloric acid. The sticky, oily precipitate is dissolved in diethyl ether, and the aqueous phase is removed. The organic phase is washed with water and saturated sodium chloride solution. After drying over magnesium sulfate, the ether is evaporated off and the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1. The crystals, which are filtered off, weigh 87.3 g after drying and correspond to the title compound (m.p. 148°-150° C.). The reaction mixture is heated to 80°-90° C. the reaction After cooling the reaction mixture is poured onto ice/water the aqueous phase is removed The organic phase is washed with water and saturated sodium chloride solution After drying over magnesium sulfate the ether is evaporated off the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1 The crystals, which are filtered off after drying