Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | 2-Benzylamino-5-nitro-benzenesulfonamide | HCID 24858397 | — |
| Katalysator | Palladium | HCID 23938 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Produkt | 2,5-Diaminobenzenesulfonamide | HCID 21888765 | 93,6% |
Reaktionsschritte
A mixture of 2-benzylamino-5-nitro-benzenesulfonamide (15 g, 48.81 mmol) and 5% palladium on activated carbon powder (wet, nominally 50% water, 6 g) in methanol (500 mL) was heated to 55° C. The mixture was degassed while stirring and the flask was charged with hydrogen gas via balloon. After stirring for 16 h under 1 atmosphere of hydrogen gas, the reaction was filtered through Celite and concentrated in vacuo to afford the desired product, 2,5-diamino-benzenesulfonamide (8.55 g, 45.67 mmol, 93.6%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ: 4.56 (2H, bs), 4.98 (2H, bs), 6.58-6.59 (2H, m), 6.87 (1H, d, J=1.6 Hz), 7.00 (2H, s). LC-MS (ESI) calcd for C6H9N3O2S 187.04, found 188.2 [M+H+].
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07582626B2 |
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| Quelldatensatz | uspto-grants-2009_09 |
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| ORD ID | ord-6435abce535e4262aba94cf48af2c38e |
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| Quellennotiz | uspto-grants-2009_09 |
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