2,3-dichlorobenzenesulfonamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:138.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 350 mL of dry xylenes was added 44 g of 2,3-dichlorobenzenesulfonamide, 23 mL of n-butyl isocyanate and 0.3 g 1,4-diazobicyclo[2.2.2]octane. This mixture was heated to reflux (138° C.) under a nitrogen atmosphere. After two hours, liquid phosgene was added to the refluxing mixture in portions over 1.5 hours at such a rate that kept the temperature between 130°-138° C. The phosgene addition was ceased when the reflux temperature had fallen to 130° C. and failed to rise, indicating that consumption of the starting material was complete (13.5 mL phosgene). The mixture was refluxed for an additional hour, cooled to room temperature, and filtered under nitrogen. Evaporation of the filtrate under reduced pressure gave 55 g of crude 2,3-dichlorobenzenesulfonyl isocyanate as a dark oil. This oil was taken up in dry acetonitrile (total solution volume 140 mL) and used as such for subsequent experiments: IR (Neat): 2250 (NCO) cm-1 This mixture was heated between 130°-138° C had fallen to 130° C. indicating that consumption of the starting material The mixture was refluxed for an additional hour cooled to room temperature filtered under nitrogen Evaporation of the filtrate under reduced pressure

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

実験手順: To a stirred solution of 60.0 g of 2,3-dichlorobenzenesulfonyl chloride in 500 mL of tetrahydrofuran at 0° C. was added 30 mL of concentrated ammonium hydroxide (30%) dropwise at a rate that maintained the temperature below 15° C. After an additional stirring period of 0.5 hr, the tetrahydrofuran was evaporated under reduced pressure. The resultant solid residue was triturated with 500 mL of water, filtered, and the collected solid washed twice with 100-mL portions of water and dried to yield 52 g of 2,3-dichlorobenzenesulfonamide as a tan solid, m.p. 210°-226° C.; IR (nujol): 3360, 3250, 1370, 1175, 1165 cm-1. maintained the temperature below 15° C the tetrahydrofuran was evaporated under reduced pressure The resultant solid residue was triturated with 500 mL of water filtered the collected solid washed twice with 100-mL portions of water dried

反応条件: temp:138.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 350 mL of dry xylenes was added 44 g of 2,3-dichlorobenzenesulfonamide, 23 mL of n-butyl isocyanate and 0.3 g 1,4-diazobicyclo[2.2.2]octane. This mixture was heated to reflux (138° C.) under a nitrogen atmosphere. After two hours, liquid phosgene was added to the refluxing mixture in portions over 1.5 hours at such a rate that kept the temperature between 130°-138° C. The phosgene addition was ceased when the reflux temperature had fallen to 130° C. and failed to rise, indicating that consumption of the starting material was complete (13.5 mL phosgene). The mixture was refluxed for an additional hour, cooled to room temperature, and filtered under nitrogen. Evaporation of the filtrate under reduced pressure gave 55 g of crude 2,3-dichlorobenzenesulfonyl isocyanate as a dark oil. This oil was taken up in dry acetonitrile (total solution volume 140 mL) and used as such for subsequent experiments: IR (Neat): 2250 (NCO) cm-1 This mixture was heated between 130°-138° C had fallen to 130° C. indicating that consumption of the starting material The mixture was refluxed for an additional hour cooled to room temperature filtered under nitrogen Evaporation of the filtrate under reduced pressure

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

実験手順: To a stirred solution of 60.0 g of 2,3-dichlorobenzenesulfonyl chloride in 500 mL of tetrahydrofuran at 0° C. was added 30 mL of concentrated ammonium hydroxide (30%) dropwise at a rate that maintained the temperature below 15° C. After an additional stirring period of 0.5 hr, the tetrahydrofuran was evaporated under reduced pressure. The resultant solid residue was triturated with 500 mL of water, filtered, and the collected solid washed twice with 100-mL portions of water and dried to yield 52 g of 2,3-dichlorobenzenesulfonamide as a tan solid, m.p. 210°-226° C.; IR (nujol): 3360, 3250, 1370, 1175, 1165 cm-1. maintained the temperature below 15° C the tetrahydrofuran was evaporated under reduced pressure The resultant solid residue was triturated with 500 mL of water filtered the collected solid washed twice with 100-mL portions of water dried

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 2,3-Dichloroquinoxaline (1.00 g, 5.02 mmol), 2,3-dichlorobenzenesulfonamide (1.41 g, 5.02 mmol) and potassium carbonate (694 mg, 5.02 mmol) were suspended in dimethyl sulfoxide (30 mL) and the mixture was stirred at 150° C. for 3 hours. The reaction mixture was slowly added to a mixture (300 ml) of a 1% aqueous acetic acid solution and ice, and the mixture was stirred for 3 hours. The resulting solid was collected by filtration and washed with water. Then, slurry purification was performed using diisopropyl ether, to give 2,3-dichloro-N-{3-chloroquinoxalin-2-yl}benzenesulfonamide (Compound AA) (1.53 g, yield: 78%). the mixture was stirred for 3 hours The resulting solid was collected by filtration washed with water Then, slurry purification

反応条件: temp:138.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 350 mL of dry xylenes was added 44 g of 2,3-dichlorobenzenesulfonamide, 23 mL of n-butyl isocyanate and 0.3 g 1,4-diazobicyclo[2.2.2]octane. This mixture was heated to reflux (138° C.) under a nitrogen atmosphere. After two hours, liquid phosgene was added to the refluxing mixture in portions over 1.5 hours at such a rate that kept the temperature between 130°-138° C. The phosgene addition was ceased when the reflux temperature had fallen to 130° C. and failed to rise, indicating that consumption of the starting material was complete (13.5 mL phosgene). The mixture was refluxed for an additional hour, cooled to room temperature, and filtered under nitrogen. Evaporation of the filtrate under reduced pressure gave 55 g of crude 2,3-dichlorobenzenesulfonyl isocyanate as a dark oil. This oil was taken up in dry acetonitrile (total solution volume 140 mL) and used as such for subsequent experiments: IR (Neat): 2250 (NCO) cm-1 This mixture was heated between 130°-138° C had fallen to 130° C. indicating that consumption of the starting material The mixture was refluxed for an additional hour cooled to room temperature filtered under nitrogen Evaporation of the filtrate under reduced pressure

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

実験手順: To a stirred solution of 60.0 g of 2,3-dichlorobenzenesulfonyl chloride in 500 mL of tetrahydrofuran at 0° C. was added 30 mL of concentrated ammonium hydroxide (30%) dropwise at a rate that maintained the temperature below 15° C. After an additional stirring period of 0.5 hr, the tetrahydrofuran was evaporated under reduced pressure. The resultant solid residue was triturated with 500 mL of water, filtered, and the collected solid washed twice with 100-mL portions of water and dried to yield 52 g of 2,3-dichlorobenzenesulfonamide as a tan solid, m.p. 210°-226° C.; IR (nujol): 3360, 3250, 1370, 1175, 1165 cm-1. maintained the temperature below 15° C the tetrahydrofuran was evaporated under reduced pressure The resultant solid residue was triturated with 500 mL of water filtered the collected solid washed twice with 100-mL portions of water dried

反応条件: temp:0.00; pressure:0.00; stir: