Hydroxylamine → N-Hydroxy-3-methanesulfonylbenzene-1-sulfonamide

HRID 1749191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749191
[NH2:1][OH:2].O.[CH3:4][S:5]([C:8]1[CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6].S(Cl)(Cl)(=O)=O>C1COCC1.C(Cl)Cl>[OH:2][NH:1][S:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([S:5]([CH3:4])(=[O:7])=[O:6])[CH:9]=1)(=[O:16])=[O:15]

Komponenten

7

Edukt 4

HCID 787HydroxylamineHCID 962WaterHCID 24648Sulfuryl chlorideHCID 2203303-(Methylsulfonyl)benzenesulfonyl chloride

Produkt 1

HCID 76901580N-Hydroxy-3-methanesulfonylbenzene-1-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of aqueous hydroxylamine (16 mL of a 50% aqueous solution, 245 mmol) in THF (150 mL) and water (25 mL) cooled to −5° C. was slowly added 3-methanesulfonylbenzene-1-sulfonyl chloride (25 g, 98 mmol) while maintaining a reaction temperature of less than 10° C. The reaction was maintained at this temperature until substantially complete consumption of the sulfonyl chloride was observed (about 5 min), after which time the reaction was diluted with DCM (250 mL), the organic portion was separated and washed twice with 50 mL of water. The aqueous extracts were combined and rewashed twice with DCM (250 mL for each wash). All of the organic portions were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a beige solid. Trituration was carried out using heptanes:EtOAc (1:1; v:v) to provide the title compound as a beige solid (14 g, yield 56%). LC-MS tR=0.90 min; High Resolution Mass Spectroscopy (HRMS): theoretical (C7H9NO5S2)=249.9844, measured=249.9833; 1H NMR (500 MHz, DMSO-d6) δ ppm 9.85 (2H, q, J=3.3 Hz), 8.31 (1H, t, J=1.6 Hz), 8.28 (1H, dt, J=7.8, 1.3 Hz), 8.14-8.19 (1H, m), 7.93 (1H, t, J=7.9 Hz), 3.32 (3H, s).

Aufarbeitung

  1. temperaturewhile maintaining a reaction temperature of less than 10° C
  2. custom(about 5 min)
  3. customthe organic portion was separated
  4. washwashed twice with 50 mL of water
  5. washeach wash)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0b0c6e79e57949a5b75c7233cc472001
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156804B2

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