Sodium hydride → 4-((1,4-Dioxan-2-yl)methoxy)-3-nitrobenzenesulfonamide

HRID 574771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574771
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][OH:8].[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]>O1CCCC1>[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][O:8][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]

Komponenten

5

Edukt 3

HCID 24758Sodium hydride2×HCID 12655091(1,4-Dioxan-2-yl)methanolHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Produkt 1

HCID 671264774-((1,4-Dioxan-2-yl)methoxy)-3-nitrobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(1,4-Dioxan-2-yl)methanol (380 mg, 3.22 mmol) in tetrahydrofuran (30 ml) was treated with sodium hydride (60%) (245 mg, 6.13 mmol) at room temperature for 30 minutes. The reaction mixture was cooled in an ice bath and 4-fluoro-3-nitrobenzenesulfonamide (675 mg, 3.06 mmol) was added. The resulting mixture was stirred at room temperature for 2 hours and another portion of sodium hydride (60%) (245 mg, 6.13 mmol) was added. The reaction mixture was stirred overnight and quenched with ice water (3 ml). The cloudy mixture was filtered and the filtrate was concentrated. The residue was triturated with methanol to give the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. stirringThe reaction mixture was stirred overnight
  3. customquenched with ice water (3 ml)
  4. filtrationThe cloudy mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-b73cc1f409a1419e87b250ca1212cd0c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034875B2

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