2-(Aminosulfonyl)-4-iodobenzoic acid methyl ester

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:

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

Procedure: 50 g of the sulfonamide obtained in Example 6 are suspended in 150 ml of 1,2-dichloroethane and the suspension is treated with 27.7 ml of thionyl chloride. The mixture is heated at the boil for 4 hours, cooled to 50°-55° C. and treated with 0.5 ml of pyridine, and phosgene is passed for 31/2 hours into the solution which has now been brought to the boil. The mixture is concentrated under reduced pressure with the exclusion of moisture. The crude sulfonyl isocyanate which remains (52.6 g) crystallises upon standing. The mixture is heated at the boil for 4 hours cooled to 50°-55° C. 2 hours The mixture is concentrated under reduced pressure with the exclusion of moisture crystallises

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

Procedure: 50 g of the sulfonamide obtained in Example 6 are suspended in 150 ml of 1,2-dichloroethane and the suspension is treated with 27.7 ml of thionyl chloride. The mixture is heated at the boil for 4 hours, cooled to 50°-55° C. and treated with 0.5 ml of pyridine, and phosgene is passed for 31/2 hours into the solution which has now been brought to the boil. The mixture is concentrated under reduced pressure with the exclusion of moisture. The crude sulfonyl isocyanate which remains (52.6 g) crystallises upon standing. The mixture is heated at the boil for 4 hours cooled to 50°-55° C. 2 hours The mixture is concentrated under reduced pressure with the exclusion of moisture crystallises

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

Procedure: 50 g of the sulfonamide obtained in Example 6 are suspended in 150 ml of 1,2-dichloroethane and the suspension is treated with 27.7 ml of thionyl chloride. The mixture is heated at the boil for 4 hours, cooled to 50°-55° C. and treated with 0.5 ml of pyridine, and phosgene is passed for 31/2 hours into the solution which has now been brought to the boil. The mixture is concentrated under reduced pressure with the exclusion of moisture. The crude sulfonyl isocyanate which remains (52.6 g) crystallises upon standing. The mixture is heated at the boil for 4 hours cooled to 50°-55° C. 2 hours The mixture is concentrated under reduced pressure with the exclusion of moisture crystallises

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

Procedure: 50 g of the sulfonamide obtained in Example 6 are suspended in 150 ml of 1,2-dichloroethane and the suspension is treated with 27.7 ml of thionyl chloride. The mixture is heated at the boil for 4 hours, cooled to 50°-55° C. and treated with 0.5 ml of pyridine, and phosgene is passed for 31/2 hours into the solution which has now been brought to the boil. The mixture is concentrated under reduced pressure with the exclusion of moisture. The crude sulfonyl isocyanate which remains (52.6 g) crystallises upon standing. The mixture is heated at the boil for 4 hours cooled to 50°-55° C. 2 hours The mixture is concentrated under reduced pressure with the exclusion of moisture crystallises

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

Procedure: 50 g of the sulfonamide obtained in Example 6 are suspended in 150 ml of 1,2-dichloroethane and the suspension is treated with 27.7 ml of thionyl chloride. The mixture is heated at the boil for 4 hours, cooled to 50°-55° C. and treated with 0.5 ml of pyridine, and phosgene is passed for 31/2 hours into the solution which has now been brought to the boil. The mixture is concentrated under reduced pressure with the exclusion of moisture. The crude sulfonyl isocyanate which remains (52.6 g) crystallises upon standing. The mixture is heated at the boil for 4 hours cooled to 50°-55° C. 2 hours The mixture is concentrated under reduced pressure with the exclusion of moisture crystallises

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 34.1 g (0.1 mol) of the sulfonamide of the formula (IV) from Example 1 and 14.7 g of K2CO3 (0.105 mol) are admixed with 10.6 g of n-butyl isocyanate (98% pure) (0.105 mol) in 250 ml of chlorobenzene, and the mixture is kept at 55 to 60° C. for 2 hours. The mixture is then stirred at 90° C. for 8.5 h. The mixture is cooled to room temperature and initially 200 ml of water and then 2n of hydrochloric acid are added until the pH has reached 1-2. The organic phase is separated off and washed free of acid using four times 50 ml of water. The solvent is removed under reduced pressure, and 43.8 g of the desired compound of the formula (I) (99.3% of theory) of melting point 128 to 130° C. remain. The mixture is cooled to room temperature The organic phase is separated off washed free of acid The solvent is removed under reduced pressure, and 43.8 g of the desired compound of the formula (I) (99.3% of theory) of melting point 128 to 130° C.

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