5-chloro-2-methoxy-N-(2-phenylethyl)benzamide

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:

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

Procedure: 4.5 ml chlorosulfonic acid were added in one portion to 6.5 g 5-Chloro-2-methoxy-N-phenethyl-benzamide. The reaction mixture was stirred at room temperature for one hour, then 100 ml dichloromethane were added and the reaction mixture was poured on ice water. The organic layer was separated washed twice with 50 ml brine and then dried over MgSO4. The solvent was removed in vacuo to obtain 5.53 g 4-[2-(5-Chloro-2-methoxy-benzoylamino)-ethyl]-benzenesulfonyl chloride. the reaction mixture was poured on ice water The organic layer was separated washed twice with 50 ml brine dried over MgSO4 The solvent was removed in vacuo

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

Procedure: 3.0 g phenethylamine, 5.0 g 5-chloro-2-methoxy-benzoic acid, and 2.72 ml triethylamine were dissolved in 100 ml dimethylformamide. 8.80 g O-((Ethoxycarbonyl)cyanomethyleneamino)-N,N,N′,N′-tetramethyluronium tetrafluoroborate were added portionwise. The reaction mixture is stirred at room temperature for three hours. 300 ml ethyl acetate were added and the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4 and then the solvent was removed in vacuo to obtain 6.5 g 5-Chloro-2-methoxy-N-phenethyl-benzamide. the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine The organic phase was dried over MgSO4 the solvent was removed in vacuo

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

Procedure: 3.0 g phenethylamine, 5.0 g 5-chloro-2-methoxy-benzoic acid, and 2.72 ml triethylamine were dissolved in 100 ml dimethylformamide. 8.80 g O-((Ethoxycarbonyl)cyanomethyleneamino)-N,N,N′,N′-tetramethyluronium tetrafluoroborate were added portionwise. The reaction mixture is stirred at room temperature for three hours. 300 ml ethyl acetate were added and the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4 and then the solvent was removed in vacuo to obtain 6.5 g 5-Chloro-2-methoxy-N-phenethyl-benzamide. the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine The organic phase was dried over MgSO4 the solvent was removed in vacuo

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

Procedure: 3.0 g phenethylamine, 5.0 g 5-chloro-2-methoxy-benzoic acid, and 2.72 ml triethylamine were dissolved in 100 ml dimethylformamide. 8.80 g O-((Ethoxycarbonyl)cyanomethyleneamino)-N,N,N′,N′-tetramethyluronium tetrafluoroborate were added portionwise. The reaction mixture is stirred at room temperature for three hours. 300 ml ethyl acetate were added and the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4 and then the solvent was removed in vacuo to obtain 6.5 g 5-Chloro-2-methoxy-N-phenethyl-benzamide. the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine The organic phase was dried over MgSO4 the solvent was removed in vacuo

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

Procedure: A process for preparing p-(2-{5-chloro-2-methoxybenzamido}ethyl)-benzene sulfonamide which comprises the steps of methylating 5-chlorosalicylic acid to methyl-5-chloro-2-methoxybenzoate, treating methyl-5-chloro-2-methoxybenzoate with phenethylamine to obtain N-phenethyl-5-chloro-2-methoxybenzamide, subjecting said N-phenethyl-5-chloro-2-methoxybenzamide to chlorosulfonation and aminolysis to yield p-(2-{5-chloro-2-methoxybenzamido}ethyl)-benzene sulfonamide.

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

Procedure: N-phenethyl-5-chloro-2-methoxybenzamide (10 g.) dissolved in 25 ml. of chloroform was cooled to -10° and 19 g. of chlorosulfonic acid was added dropwise, maintaining the temperature at -10° to 0°. After the addition was complete the mixture was allowed to rise to room temperature and it was poured onto cracked ice. The crude sulfonic acid was filtered and 7.3 g. (57%) was obtained. A sample recrystallized for analysis from alcohol-acetonitrile melted at 188°-189°. Anal. Calcd. for C16H16ClNO5S: C, 51.94; H, 4.36; Cl, 9.58; N, 3.79; S, 8.67. Found: C, 50.10; H, 4.27; Cl, 9.93; N, 4.04; S, 8.84. maintaining the temperature at -10° to 0° After the addition to rise to room temperature it was poured The crude sulfonic acid was filtered (57%) was obtained A sample recrystallized for analysis from alcohol-acetonitrile melted at 188°-189°