1,3-dihydro-2lambda6,1,3-benzothiadiazole 2,2-dioxide

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

Procedure: A solution of 1,2-phenylenediamine (91 mg, 0.84 mmol) and sulfamide (81 mg, 0.84 mmol) in diglyme (2.5 ml) is stirred at 155° C. for 1.5 h. After cooling to RT, the reaction solution is poured into ice-water (15 ml) and the product is extracted with ethyl acetate. The solvent is distilled off under reduced pressure and the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene). the product is extracted with ethyl acetate The solvent is distilled off under reduced pressure the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene)

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

Procedure: Sodium hydride (5 g) was added to a solution of 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (10 g) obtained in Reference Example 126 in dimethylformamide (100 ml), the mixture was stirred at room temperature for 1 hour, methyl iodide was added, and the mixture was stirred at room temperature for 18 hours. Water (200 g) was poured into the reaction mixture, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (9.9 g). Further recrystallization from water-ethyl acetate afforded the title compound as colorless crystals (9.0 g). the mixture was stirred at room temperature for 18 hours extracted with ethyl acetate washed with brine The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure

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

Procedure: Sodium hydride (5 g) was added to a solution of 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (10 g) obtained in Reference Example 126 in dimethylformamide (100 ml), the mixture was stirred at room temperature for 1 hour, methyl iodide was added, and the mixture was stirred at room temperature for 18 hours. Water (200 g) was poured into the reaction mixture, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (9.9 g). Further recrystallization from water-ethyl acetate afforded the title compound as colorless crystals (9.0 g). the mixture was stirred at room temperature for 18 hours extracted with ethyl acetate washed with brine The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure

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

Procedure: A solution of orthophenylenediamine (20 g) and sulfamide (20.4 g) in diglyme (200 ml) was stirred at 160° C. for 2 hours, the reaction mixture was cooled to room temperature, water (200 g) was poured thereto, hydrochloric acid was added until pH 1, extracted with ethyl acetate, and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (14.2 g). Further recrystallization from ethanol-diethyl ether afforded the title compound as colorless crystals (13.2 g). extracted with ethyl acetate washed with 1N hydrochloric acid The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure

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

Procedure: Sodium hydride (5 g) was added to a solution of 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (10 g) obtained in Reference Example 126 in dimethylformamide (100 ml), the mixture was stirred at room temperature for 1 hour, methyl iodide was added, and the mixture was stirred at room temperature for 18 hours. Water (200 g) was poured into the reaction mixture, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (9.9 g). Further recrystallization from water-ethyl acetate afforded the title compound as colorless crystals (9.0 g). the mixture was stirred at room temperature for 18 hours extracted with ethyl acetate washed with brine The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure

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

Procedure: A solution of orthophenylenediamine (20 g) and sulfamide (20.4 g) in diglyme (200 ml) was stirred at 160° C. for 2 hours, the reaction mixture was cooled to room temperature, water (200 g) was poured thereto, hydrochloric acid was added until pH 1, extracted with ethyl acetate, and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (14.2 g). Further recrystallization from ethanol-diethyl ether afforded the title compound as colorless crystals (13.2 g). extracted with ethyl acetate washed with 1N hydrochloric acid The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure

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

Procedure: A solution of orthophenylenediamine (20 g) and sulfamide (20.4 g) in diglyme (200 ml) was stirred at 160° C. for 2 hours, the reaction mixture was cooled to room temperature, water (200 g) was poured thereto, hydrochloric acid was added until pH 1, extracted with ethyl acetate, and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (14.2 g). Further recrystallization from ethanol-diethyl ether afforded the title compound as colorless crystals (13.2 g). extracted with ethyl acetate washed with 1N hydrochloric acid The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure

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

Procedure: A solution of 1,2-phenylenediamine (91 mg, 0.84 mmol) and sulfamide (81 mg, 0.84 mmol) in diglyme (2.5 ml) is stirred at 155° C. for 1.5 h. After cooling to RT, the reaction solution is poured into ice-water (15 ml) and the product is extracted with ethyl acetate. The solvent is distilled off under reduced pressure and the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene). the product is extracted with ethyl acetate The solvent is distilled off under reduced pressure the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene)

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

Procedure: A solution of 1,2-phenylenediamine (91 mg, 0.84 mmol) and sulfamide (81 mg, 0.84 mmol) in diglyme (2.5 ml) is stirred at 155° C. for 1.5 h. After cooling to RT, the reaction solution is poured into ice-water (15 ml) and the product is extracted with ethyl acetate. The solvent is distilled off under reduced pressure and the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene). the product is extracted with ethyl acetate The solvent is distilled off under reduced pressure the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene)

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

Procedure: Sodium hydride (5 g) was added to a solution of 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (10 g) obtained in Reference Example 126 in dimethylformamide (100 ml), the mixture was stirred at room temperature for 1 hour, methyl iodide was added, and the mixture was stirred at room temperature for 18 hours. Water (200 g) was poured into the reaction mixture, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (9.9 g). Further recrystallization from water-ethyl acetate afforded the title compound as colorless crystals (9.0 g). the mixture was stirred at room temperature for 18 hours extracted with ethyl acetate washed with brine The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure

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

Procedure: A solution of orthophenylenediamine (20 g) and sulfamide (20.4 g) in diglyme (200 ml) was stirred at 160° C. for 2 hours, the reaction mixture was cooled to room temperature, water (200 g) was poured thereto, hydrochloric acid was added until pH 1, extracted with ethyl acetate, and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (14.2 g). Further recrystallization from ethanol-diethyl ether afforded the title compound as colorless crystals (13.2 g). extracted with ethyl acetate washed with 1N hydrochloric acid The organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure

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

Procedure: A solution of 1,2-phenylenediamine (91 mg, 0.84 mmol) and sulfamide (81 mg, 0.84 mmol) in diglyme (2.5 ml) is stirred at 155° C. for 1.5 h. After cooling to RT, the reaction solution is poured into ice-water (15 ml) and the product is extracted with ethyl acetate. The solvent is distilled off under reduced pressure and the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene). the product is extracted with ethyl acetate The solvent is distilled off under reduced pressure the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene)