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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.
N-Acetylsulfanilamide is a sulfonamide derivative that exerts antibacterial activity by inhibiting bacterial dihydropteroate synthase (DHPS), thus preventing folate synthesis. It is commonly used to treat bacterial infections, particularly urinary tract infections, and to study mechanisms of antimicrobial resistance.
Synonyms: 4-Acetamidobenzenesulfonamide; APAS; NSC 406839
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| CAS No. : | 121-61-9 |
| Formula : | C8H10N2O3S |
| M.W : | 214.24 |
| SMILES Code : | CC(NC1=CC=C(S(=O)(N)=O)C=C1)=O |
| Synonyms : |
4-Acetamidobenzenesulfonamide; APAS; NSC 406839
|
| English Name : | 4-Acetamidobenzenesulfonamide |
| MDL No. : | MFCD00035784 |
| InChI Key : | PKOFBDHYTMYVGJ-UHFFFAOYSA-N |
| Pubchem ID : | 8482 |
* 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 |
|---|---|---|
| With copper; potassium carbonate at 200℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With pyridine; copper; sodium carbonate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | In acetone at 30℃; for 6h; | 3.1.2. Synthesis General procedure: Compound 1a (10 mmol) and anhydrous acetone (30 mL) in a round bottom flask, reacted with acetic anhydride (12 mmol) and ethyl chloroformate (15 mmol) at 30 °C for 6 h with stirring. Hydrochloric acid (1 M) was then added to the reaction mixture to adjust the pH to 1, the acetone removed by vacuum evaporation, and the aqueous phase was extracted with ethyl acetate (15 mL×3). Ethyl acetate phases were combined, washed twice with saturated NaCl solution, and dried with MgSO4. The extracte dethyl acetate solution was heated to 60 °C. Petroleum ether was added slowly to gradually produce a precipitate, transferred it to room temperature and cooled down, filtered and dried to obtain products 2a and 2b (Ghasemi et al. 2016; Dong et al. 2019; Wei et al. 2016). Compound 1b (10 mmol) and acetone (30 mL) reacted at 60 °C for 5 h. Product 2c was recrystallized with petroleum ether after the solvent was removed by evaporation under reduced pressure (Hebeisen et al. 2011). Compound 2c: 1H NMR (500 MHz, DMSO-d6, δ), 10.31 (s, 1H), 9.91 (s, 1H), 7.79- 7.71 (m, 4H), 2.08 (s, 3H), 1.77-1.78 (s, 6H). |
| 95% | In acetone at 30℃; for 6h; | 3.1.2. Synthesis General procedure: Compound 1a (10 mmol) and anhydrous acetone (30 mL) in a round bottom flask, reacted with acetic anhydride (12 mmol) and ethyl chloroformate (15 mmol) at 30 °C for 6 h with stirring. Hydrochloric acid (1 M) was then added to the reaction mixture to adjust the pH to 1, the acetone removed by vacuum evaporation, and the aqueous phase was extracted with ethyl acetate (15 mL×3). Ethyl acetate phases were combined, washed twice with saturated NaCl solution, and dried with MgSO4. The extracte dethyl acetate solution was heated to 60 °C. Petroleum ether was added slowly to gradually produce a precipitate, transferred it to room temperature and cooled down, filtered and dried to obtain products 2a and 2b (Ghasemi et al. 2016; Dong et al. 2019; Wei et al. 2016). Compound 1b (10 mmol) and acetone (30 mL) reacted at 60 °C for 5 h. Product 2c was recrystallized with petroleum ether after the solvent was removed by evaporation under reduced pressure (Hebeisen et al. 2011). Compound 2c: 1H NMR (500 MHz, DMSO-d6, δ), 10.31 (s, 1H), 9.91 (s, 1H), 7.79- 7.71 (m, 4H), 2.08 (s, 3H), 1.77-1.78 (s, 6H). |
| 93% | With magnetic composite Fe3O4 Diatomite earth In tetrahydrofuran at 50℃; for 1h; | General procedure for N-acylation of sulfonamides According to the Scheme 1, 4 mmol of N-(4-Sulfamoylphenyl) acetamide was treated with acetic anhydride (4 mmol) in glacial acetic acid (10 mL). The mixture was stirred at 50°C for the predetermined time. The progress of the reaction was monitored by TLC analysis. After the completion of the reaction, the precipitate was collected by filtration and washed with water. The impure precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration to afford N-(4-acetamidophenylsulfonyl)acetamide a1 as the white solid (0.97 g, 95%). The catalytic activities of different heterogeneous catalysts were determined by reactions performed in THF using a 1:1 molar ratio of sulfonamide to acetic anhydride or benzoyl chloride. In a typical route, N-(4-sulfamoylphenyl) acetamide (4 mmol) was treated with acetic anhydride (4 mmol) in the presence of catalyst (0.1 g) in THF (10 mL). After the appropriate time, the catalyst was separated with an external magnetic field, the solvent was evaporated by rotary evaporator. The precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration and was washed with distilled water to afford N-(4-acetamidophenylsulfonyl)acetamide as the white solid (0.95 g, 93%). |
| With pyridine |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With Copper; potassium carbonate at 180℃; Erwaermen des Reaktionsprodukts mit wss. Natronlauge; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With pyridine |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With Copper; potassium carbonate at 180℃; Erwaermen des Reaktionsprodukts mit wss. Natronlauge; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate In diphenylether Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99.5% | With thionyl chloride In methanol for 2.5h; Reflux; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 4 h / 0 - 20 °C 2: hydrazine hydrate / ethanol / 1.5 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With ammonium hydroxide In water; acetone at 65℃; for 2.5h; |