2-propoxybenzamide

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

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

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

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

Procedure: Chlorosulphonic acid (200 ml.), cooled to 10° C., was treated with 2-propoxybenzamide (60 g.) in aliquots with stirring during 45 minutes. When complete solution had occurred, the solution was allowed to stand at room temperature for 24 hours. The resulting yellow-brown solution was then added dropwise, with stirring, to ice (1.5 kg.), keeping the temperature at or below 0° C. The precipitated solid was filtered off, washed with ice-cold water, and sucked dry. The solid was then dissolved in dichloromethane (approximately 2 liters), any water still present was separated off, and the organic layer was dried over calcium chloride and then over magnesium sulphate. Most of the dichloromethane was removed in vacuo, the low volume residue was treated with petroleum ether (b.p. 40° - 60° C.) and the precipitated solid was filtered off, to give crude 5-chlorosulphonyl-2-propoxybenzamide (81 g.), m.p. 122° - 129° C. to stand at room temperature for 24 hours The resulting yellow-brown solution was then added dropwise below 0° C The precipitated solid was filtered off washed with ice-cold water sucked dry The solid was then dissolved in dichloromethane (approximately 2 liters) any water still present was separated off the organic layer was dried over calcium chloride Most of the dichloromethane was removed in vacuo the low volume residue was treated with petroleum ether (b.p. 40° - 60° C.) the precipitated solid was filtered off

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

Procedure: Chlorosulphonic acid (200 ml.), cooled to 10° C., was treated with 2-propoxybenzamide (60 g.) in aliquots with stirring during 45 minutes. When complete solution had occurred, the solution was allowed to stand at room temperature for 24 hours. The resulting yellow-brown solution was then added dropwise, with stirring, to ice (1.5 kg.), keeping the temperature at or below 0° C. The precipitated solid was filtered off, washed with ice-cold water, and sucked dry. The solid was then dissolved in dichloromethane (approximately 2 liters), any water still present was separated off, and the organic layer was dried over calcium chloride and then over magnesium sulphate. Most of the dichloromethane was removed in vacuo, the low volume residue was treated with petroleum ether (b.p. 40° - 60° C.) and the precipitated solid was filtered off, to give crude 5-chlorosulphonyl-2-propoxybenzamide (81 g.), m.p. 122° - 129° C. to stand at room temperature for 24 hours The resulting yellow-brown solution was then added dropwise below 0° C The precipitated solid was filtered off washed with ice-cold water sucked dry The solid was then dissolved in dichloromethane (approximately 2 liters) any water still present was separated off the organic layer was dried over calcium chloride Most of the dichloromethane was removed in vacuo the low volume residue was treated with petroleum ether (b.p. 40° - 60° C.) the precipitated solid was filtered off

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

Procedure: The title compound (74% yield) was prepared from 2-n-propoxybenzamide in a manner similar to that described for the preparation of 2-ethoxybenzamidine methyl sulfate in Preparation 6 above.

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

Procedure: A solution of triethyloxonium fluoroborate (33.0 g., 0.175 mole) in methylene chloride (75 ml.) was added during 10 minutes to a stirred solution of 2-n-propoxybenzamide (31.3 g., 0.175 mole) in methylene chloride (150 ml.). The solution was stirred for an additional 18 hours at room temperature. The solution was concentrated to about one-fifth volume and was diluted with diethyl ether to precipitate the ethyl 2-n-propoxybenzimidate fluoroborate (44.0 g., 85% yield), m.p. 108°-112°. The solution was concentrated to about one-fifth volume was diluted with diethyl ether

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

Procedure: A solution of triethyloxonium fluoroborate (33.0 g., 0.175 mole) in methylene chloride (75 ml.) was added during 10 minutes to a stirred solution of 2-n-propoxybenzamide (31.3 g., 0.175 mole) in methylene chloride (150 ml.). The solution was stirred for an additional 18 hours at room temperature. The solution was concentrated to about one-fifth volume and was diluted with diethyl ether to precipitate the ethyl 2-n-propoxybenzimidate fluoroborate (44.0 g., 85% yield), m.p. 108°-112°. The solution was concentrated to about one-fifth volume was diluted with diethyl ether

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

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

Procedure: A 130 gm. portion of salicylamide in 500 ml. of ethanol is reacted with 52.4 gm. of sodium methoxide and 164.9 gm. of 1-iodopropane by heating at reflux. The mixture is cooled, precipitated in 1500 ml. of water and the solid is recrystallized from hot ethanol giving o-propoxybenzamide. at reflux The mixture is cooled precipitated in 1500 ml of water and the solid is recrystallized from hot ethanol

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

Procedure: A 130 gm. portion of salicylamide in 500 ml. of ethanol is reacted with 52.4 gm. of sodium methoxide and 164.9 gm. of 1-iodopropane by heating at reflux. The mixture is cooled, precipitated in 1500 ml. of water and the solid is recrystallized from hot ethanol giving o-propoxybenzamide. at reflux The mixture is cooled precipitated in 1500 ml of water and the solid is recrystallized from hot ethanol

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

Procedure: To a cooled (ice bath) solution of 2-n-propoxybenzamide (1.00 g., 5.61 mmoles) in dry N,N-dimethylformamide (4 ml.) was added ethyl ethoxymethylenecyanoacetate (0.94 g., 5.61 mmoles). Twenty minutes later sodium azide (0.447 g., 6.88 mmoles) and ammonium chloride (0.368 g., 6.88 mmoles were added. The ice bath was removed and the mixture heated by means of an oil bath maintained at 127° for 30 hours. The cooled mixture was poured into ice-water (400 ml.) and acidified with 6N hydrochloric acid. The collected solid (0.93 g.), m.p. 245°-248° (decomp) was recrystallized from 2-methoxyethanol to give the title compound (0.69 g., 41%) m.p. 256°-257° (decomp). , 6.88 mmoles were added The ice bath was removed the mixture heated by means of an oil bath maintained at 127° for 30 hours The cooled mixture was poured into ice-water (400 ml.) The collected solid (0.93 g.), m.p. 245°-248° (decomp) was recrystallized from 2-methoxyethanol