Structure of 98-32-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 98-32-8 |
| Formula : | C6H8N2O3S |
| M.W : | 188.20 |
| SMILES Code : | C1=C(C(=CC=C1[S](N)(=O)=O)O)N |
| MDL No. : | MFCD00035782 |
| InChI Key : | AVQFHKYAVVQYQO-UHFFFAOYSA-N |
| Pubchem ID : | 66814 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92% | In tetrahydrofuran; at 20℃; for 5h; | To a solution of 3-amino-4-hydroxy-benzenesulfonamide (5.00 g, 26.6 mmol, 1.0 equiv) in anhydrous THF (250 mL) was added slowly thiophosgene (3.67 g, 2.43 mL, 31.9 mmol, 1.2 equiv) via syringe pump over a time period of 1 h. After stirring for 4 h at rt, excess thiophosgene was quenched by addition of a conc. solution of ammonium chloride (100 mL) and the majority of solvent removed by evaporation under reduced pressure. The residue was extracted with ethyl acetate (3.x.100 mL) and the combined organic phases dried over MgSO4 yielding 6.1 g (92percent) of crude product, which was used in the subsequent reaction step without further purification. 1H NMR (300 MHz, DMSO): delta 7.51 (br s, 2H), 7.68 (s, 1H), 7.70 (d, J=7.7 Hz, 1H), 7.78 (d, J=7.7 Hz, 1H), 14.21 (br s, 1H). 13C NMR (75 MHz, DMSO): delta 106.29, 108.47, 120.06, 129.91, 139.54, 148.16, 179.38. MS (ISP): 230.9 [M+H]+. |
[ 98-32-8 ]
[ 90008-07-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In tetrahydrofuran; for 4h;Heating / reflux; | 500 mg of the product of 22A and 400 mg of 2-amino-5-sulfonamido phenol were dissolved in 100 ml THF and refluxed for 4 hours. The obtained crystals were washed with acetone to obtain 225 mg of a product melting at 312° C. Microanalysis theory (percent): C, 40.0; H, 2.64; N, 10.0. obtained (percent): C, 40.0; H, 2.60; N, 9.85. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 42% | With ammonium nitrate; sulfuric acid; In water; at 0℃; for 0.25h; | General procedure: NH4NO3 (1.1 equiv) was added portion wise to a solution of aromaticsulfonamides A?H (1.2 mmol, 1.0 equiv) in 95percent H2SO4 (1 ml)at 0 C. The suspension was stirred at the same temperature for15 min, then quenched with slush (8 ml) and the formed precipitatewas filtered-off and washed with cold water. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Afterthe addition of 56.5 parts of 400 parts of water 3-amino-4-hydroxyphenylsulfone amide, By addition of 25percent sodium hydroxide aqueous solution to obtainan aqueous solution of pH 7.5 ~ 8.0 from. To this aqueous solution, afteraddition of 35percent hydrochloric acid 78.2 parts, and 5 ~ 10 in an ice bath, was added 56.9 parts of a 40percent aqueous solution ofsodium nitrite, the mixture was reacted for about 30 minutes at the sametemperature, further stirredfor 5 minutes with the addition of 5.0 parts of sulfamic acid to give a diazoreaction solution. Onthe other hand, after adding to 400 parts of water3-methoxy-methyl-1-phenyl-pyrazolone and 60 parts, by the addition of 25percentsodium hydroxide aqueous solution to obtain an aqueous solution of pH8.5 ~ 9.0.Further with 5 ~ 10 in an ice bath. To this aqueous solution, by the addition at any time of 25percent sodiumhydroxide aqueous solution pH 8.5 to 9.0 Keeping the temperature 5 ~ 10 , diazo reaction solution obtained above was added dropwise over 15minutes, while an additional 3 hours while maintaining the pH 8.5 ~ 9.0, atemperature of 5 ~ 10 It reacted, and the precipitated solid was separated by filtration thefollowing formula the compound 376 parts of the formula (6) as a wet cake. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 200 ml beaker<strong>[98-32-8]2-aminophenol-4-sulfonamide</strong>(Manufactured by Tokyo Chemical Industry Co., Ltd.) 6.6 parts and water 50 parts were charged,35percent hydrochloric acid water was added dropwise to adjust the pH to 1.0 or less.7.3 parts of a 40percent sodium nitrite aqueous solution was added dropwise at a liquid temperature of 10 ° C. or lower,And the mixture was stirred at 10 ° C. or less for 1 hour.Next, this reaction solution was added to a pyridone compound represented by the following formula (101)8 parts were dissolved in 100 parts of water,While maintaining the pH at 8.5 to 9.0, at a temperature of 10 ° C. or lower, in a suspension adjusted to pH 9 with 15percent sodium carbonate aqueous solution. After completion of the dropwise addition, the reaction solution was stirred overnight. Subsequently, the reaction solution was heated to 60 to 70 ° C.,The mixture was stirred while maintaining the pH at 6 to 7, and the precipitated crystals were collected by filtration and dried to obtain 6.1 parts of a dye intermediate represented by the following formula (102). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| To 100 parts of 18 ° C ~ 22 ° C water was added 3.41 parts of 3-amino-4-methoxy benzoic acid and 4.71 Parts of 35percent hydrochloric acid. The resulting solution was cooled to 5 ° C. Thereto was added 1.46 parts of sodium nitrite, And the diazotization mixture for 2 hours to obtain a reaction solution. To 160 parts 18° C ~ 22 ° C water was added 12.22 parts of 7,7'-imino-bis (4-hydroxy-2-sulfonic acid), and treated with Sodium carbonate The pH of the mixture was adjusted to 7.0, and the mixture was cooled to 5 ° C. By the addition And sodium carbonate while maintaining the pH of 7.0 to 7.5, with two hours to the resulting solution was added the above reaction It should be added. Then, the mixture was further stirred for 5 hours. 80 parts of water were added to 3.76 parts of 3- amino-4-hydroxybenzenesulfonamide and 4.88 parts of 35percent hydrochloric acid, and the solution was cooled to 0 ° C. Its 1.46 parts of sodium nitrite was added, and the mixture was subjected to diazotization of 2 hours, thereby obtaining While the reaction solution was then maintained by addition of sodium carbonate to pH 7.0 to 8.0, with 2 H it was added to the above reaction solution was stirred for 5 hours after the. By the addition of sodium carbonate while pH was maintained at 8.0 to 9.0, and the solution was stirred for a further 2 hours. By the addition of 100 parts of Salt and the reaction solution was subjected to salting, and the precipitate was collected by filtration (i.e., the Compounds of formula (11) shown below represented). |
[ 3425-46-5 ]
[ 14002-51-8 ]
[ 98-32-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 69% | General procedure: Potassium selenocyanate (0.14 g, 1.0 mmol) dissolved inacetone (5.0 mL) was treated with the appropriate acyl chloride1a?i (1.0 mmol). The reaction mixture was stirred at r.t. for15 min, followed by addition of appropriate aminobenzensulfonamide(2?6) (1.0 mmol) and stirred for 40 min at the same temperature.After this time the mixture was quenched with H2O and theformed precipitate was filtered-off and dried on air. The obtainedproducts 7?22 were used as they are. |
[ 3425-46-5 ]
[ 98-32-8 ]
[ 5538-51-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | General procedure: Potassium selenocyanate (0.14 g, 1.0 mmol) dissolved inacetone (5.0 mL) was treated with the appropriate acyl chloride1a?i (1.0 mmol). The reaction mixture was stirred at r.t. for15 min, followed by addition of appropriate aminobenzensulfonamide(2?6) (1.0 mmol) and stirred for 40 min at the same temperature.After this time the mixture was quenched with H2O and theformed precipitate was filtered-off and dried on air. The obtainedproducts 7?22 were used as they are. |
[ 21900-25-4 ]
[ 3425-46-5 ]
[ 98-32-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | General procedure: Potassium selenocyanate (0.14 g, 1.0 mmol) dissolved inacetone (5.0 mL) was treated with the appropriate acyl chloride1a?i (1.0 mmol). The reaction mixture was stirred at r.t. for15 min, followed by addition of appropriate aminobenzensulfonamide(2?6) (1.0 mmol) and stirred for 40 min at the same temperature.After this time the mixture was quenched with H2O and theformed precipitate was filtered-off and dried on air. The obtainedproducts 7?22 were used as they are. |
[ 17754-90-4 ]
[ 98-32-8 ]
[ 105-56-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 68% | In butan-1-ol; for 7h;Reflux; | General procedure: Salicylaldehyde (2 mmol), ethyl cyanoacetate (2 mmol), and o-aminophenol(2 mmol) were mixed in n-BuOH (20 mL), and the solution was refluxed for 7 h.The solvent was removed, and the residue was suspended in EtOH (10 mL) and stirred with 1 percent NaOH (10 mL) for 30 min. After filtration and washing with water,the product was obtained as yellow solid. |
[ 673-22-3 ]
[ 98-32-8 ]
[ 105-56-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 58% | In butan-1-ol; for 7h;Reflux; | General procedure: Salicylaldehyde (2 mmol), ethyl cyanoacetate (2 mmol), and o-aminophenol(2 mmol) were mixed in n-BuOH (20 mL), and the solution was refluxed for 7 h.The solvent was removed, and the residue was suspended in EtOH (10 mL) and stirred with 1 percent NaOH (10 mL) for 30 min. After filtration and washing with water,the product was obtained as yellow solid. |
[ 98-32-8 ]
[ 105-56-6 ]
[ 1761-61-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 68% | In butan-1-ol; for 7h;Reflux; | General procedure: Salicylaldehyde (2 mmol), ethyl cyanoacetate (2 mmol), and o-aminophenol(2 mmol) were mixed in n-BuOH (20 mL), and the solution was refluxed for 7 h.The solvent was removed, and the residue was suspended in EtOH (10 mL) and stirred with 1 percent NaOH (10 mL) for 30 min. After filtration and washing with water,the product was obtained as yellow solid. |