Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | 2,5-Diaminobenzenesulfonamide | HCID 21888765 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68841809 | HCID 68841809 | 68% |
Reaction Steps
2,5-Diamino-benzenesulfonamide (288 mg, 1.5 mol, prepared according to the procedure as described in Goldfarb A. R. et. al., J. Amer. Chem. Soc. 1943, 65, 738) in dichloromethane (5 mL) and pyridine (5 mL) at 0° C. was treated dropwise with methanesulfonyl chloride (119 μL, 1.5 mmol) over 3 minutes. The reaction mixture was warmed to 25° C. and stirred for 18 hours and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with methanol in dichloromethane to yield the title compound (68% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.21 (m, 1H), 7.45 (d, J=2.57 Hz, 1H), 7.29 (s, 2H), 7.13 (dd, J=8.64, 2.39 Hz, 1H), 6.78 (d, J=8.82 Hz, 1H), 5.80 (s, 1H), 3.39 (s, 1H), 2.87 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07517876B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-1cdbbb2a900c40c1ac9fc9714348c9c6 |
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| Source note | uspto-grants-2009_04 |
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