Methyl 4-aMino-2-sulfaMoylbenzoate

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

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

Procedure: In 3 ml of acetic acid, 1 mmol of methyl 4-amino-2-(aminosulfonyl)benzoate and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 80° C. for 40 hours. Acetic acid was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water to the oily residue. After the mixture thus formed was stirred for 2 hours, the resulting precipitate was collected by filtration and then dried in air. Yield: 43%. Its physiocochemical properties are shown in Table 8. Acetic acid was then distilled off from the reaction mixture followed by the addition of 20 ml of ice water to the oily residue After the mixture thus formed the resulting precipitate was collected by filtration dried in air

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 3 ml of acetic acid, 300 mg (1.3 mmol) of methyl 4-amino2-(aminosulfonyl)benzoate and 0.23 ml of 2,5-dimethoxytetrahydrofuran were dissolved, followed by stirring at 110° C. for 1.5 hours. Acetic acid was then distilled off, followe by the addition of 30 ml of ice water. After the mixture thus obtained wa stirred for 20 minutes, the resulting precipitate was collected by filtration and dried in air. The brown solid thus obtained was purified b column chromatography, using silica gel ("Wako Gel C300", trade name; product of Wako Pure Chemical Industries, Ltd.) and dichloromethane, thereby obtaining the title compound as a white solid. Yield: 175.7 mg (48%). Its physicochemical properties are shown in Table 7. Acetic acid was then distilled off followe by the addition of 30 ml of ice water After the mixture thus obtained wa stirred for 20 minutes the resulting precipitate was collected by filtration dried in air The brown solid thus obtained was purified b column chromatography

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

Procedure: In 3 ml of acetic acid, 1 mmol of methyl 4-amino-2-(aminosulfonyl)benzoate and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 80° C. for 40 hours. Acetic acid was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water to the oily residue. After the mixture thus formed was stirred for 2 hours, the resulting precipitate was collected by filtration and then dried in air. Yield: 43%. Its physicochemical properties are shown in Table 8. Acetic acid was then distilled off from the reaction mixture followed by the addition of 20 ml of ice water to the oily residue After the mixture thus formed the resulting precipitate was collected by filtration dried in air

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

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

Procedure: In 3 ml of acetic acid, 1 mmol of methyl 4-amino-2-(aminosulfonyl)benzoate and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 80° C. for 40 hours. Acetic acid was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water to the oily residue. After the mixture thus formed was stirred for 2 hours, the resulting precipitate was collected by filtration and then dried in air. Yield: 43%. Its physicochemical properties are shown in Table 8. Acetic acid was then distilled off from the reaction mixture followed by the addition of 20 ml of ice water to the oily residue After the mixture thus formed the resulting precipitate was collected by filtration dried in air

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

Procedure: In 3 ml of acetic acid, 1 mmol of methyl 4-amino-2-(aminosulfonyl)benzoate and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 80° C. for 40 hours. Acetic acid was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water to the oily residue. After the mixture thus formed was stirred for 2 hours, the resulting precipitate was collected by filtration and then dried in air. Yield: 43%. Its physicochemical properties are shown in Table 8. Acetic acid was then distilled off from the reaction mixture followed by the addition of 20 ml of ice water to the oily residue After the mixture thus formed the resulting precipitate was collected by filtration dried in air

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1000 g (4.34 mol) of methyl 4-amino-2-aminosulfonylbenzoate and 3400 ml of H2O are admixed rapidly with 3700 ml of concentrated hydrochloric acid (37% strength). 10 ml of toluene are added to this mixture. The mixture is cooled to 15° C. and a solution of 315 g of NaNO2 (4.56 mol) in 1740 ml of H2O is added within a period of 1 h (h=hour) at 15-20° C. Stirring is continued for 1 h and the excess of nitrite is destroyed using amidosulfonic acid. In a second vessel, 1082 g of potassium iodide (6.51 mol) and 7000 ml of H2O are initially charged. At 15 to 20° C., the diazonium salt solution is added over a period of 1 to 2 h. The resulting suspension is diluted with 10 liters of H2O and the precipitate is filtered off with suction. The filter cake is then washed free of iodine using a mixture of 435 g of Na2S2O5 in 8.5 liters of H2O, and then washed neutral with 25 liters of H2O. The compound of the formula (IV) is obtained in a quantity of 1771 g (moist). After drying at 50° C. in vacuo (=under reduced pressure), 1403 g (94.8% of theory) of methyl 4-iodo-2- aminosulfonylbenzoate (sulfonamide of the formula IV) of a melting point of 175-177° C. are obtained. the excess of nitrite is destroyed the precipitate is filtered off with suction The filter cake is then washed free of iodine using a mixture of 435 g of Na2S2O5 in 8.5 liters of H2O washed neutral with 25 liters of H2O

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

Procedure: In 3 ml of acetic acid, 1 mmol of methyl 4-amino-2-(aminosulfonyl)benzoate and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 80° C. for 40 hours. Acetic acid was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water to the oily residue. After the mixture thus formed was stirred for 2 hours, the resulting precipitate was collected by filtration and then dried in air. Yield: 43%. Its physiocochemical properties are shown in Table 8. Acetic acid was then distilled off from the reaction mixture followed by the addition of 20 ml of ice water to the oily residue After the mixture thus formed the resulting precipitate was collected by filtration dried in air

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 3 ml of acetic acid, 300 mg (1.3 mmol) of methyl 4-amino2-(aminosulfonyl)benzoate and 0.23 ml of 2,5-dimethoxytetrahydrofuran were dissolved, followed by stirring at 110° C. for 1.5 hours. Acetic acid was then distilled off, followe by the addition of 30 ml of ice water. After the mixture thus obtained wa stirred for 20 minutes, the resulting precipitate was collected by filtration and dried in air. The brown solid thus obtained was purified b column chromatography, using silica gel ("Wako Gel C300", trade name; product of Wako Pure Chemical Industries, Ltd.) and dichloromethane, thereby obtaining the title compound as a white solid. Yield: 175.7 mg (48%). Its physicochemical properties are shown in Table 7. Acetic acid was then distilled off followe by the addition of 30 ml of ice water After the mixture thus obtained wa stirred for 20 minutes the resulting precipitate was collected by filtration dried in air The brown solid thus obtained was purified b column chromatography

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

Procedure: In 3 ml of acetic acid, 1 mmol of methyl 4-amino-2-(aminosulfonyl)benzoate and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 80° C. for 40 hours. Acetic acid was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water to the oily residue. After the mixture thus formed was stirred for 2 hours, the resulting precipitate was collected by filtration and then dried in air. Yield: 43%. Its physicochemical properties are shown in Table 8. Acetic acid was then distilled off from the reaction mixture followed by the addition of 20 ml of ice water to the oily residue After the mixture thus formed the resulting precipitate was collected by filtration dried in air