Hydrochloric Acid → 3-nitro-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 624388

Reaktionsgleichung

Reaktionsgleichung von HRID 624388
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23].Cl>O1CCCC1.O>[N+:22]([C:13]1[CH:14]=[C:15]([S:18]([NH2:21])(=[O:19])=[O:20])[CH:16]=[CH:17][C:12]=1[O:8][CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)([O-:24])=[O:23]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Produkt 1

HCID 671264583-nitro-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(Tetrahydro-2H-pyran-4-yl)methanol (2.0 g) in tetrahydrofuran (20 mL) was treated with 60% NaH (1.377 g). The solution was stirred for 20 minutes at room temperature. To this solution was added 4-fluoro-3-nitrobenzenesulfonamide (2.84 g) portion-wise. The reaction was stirred for another 2 hours. The mixture was poured into water, neutralized with 10% HCl, and extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel eluting with 20%-60% ethyl acetate in hexanes.

Aufarbeitung

  1. stirringThe reaction was stirred for another 2 hours
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with flash column chromatography on silica gel eluting with 20%-60% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8308bbadc8224fd7a5982172201481d3
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303025B2

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