Benzenesulfonyl chloride → 4-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-indazole

HRID 896295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896295
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][NH:9]2.[H-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][N:9]2[S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23]

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 22326703HCID 22326703, Verbindung

Produkt 1

HCID 120184394-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 4-(2-chloroethoxy)-1H-indazole (1.1 g, 5.59 mmol) in tetrahydrofuran is treated with NaH (0.335 g, 60% in mineral oil, 8.39 mmol) under nitrogen at room temperature, stirred for 30 minutes, treated with benzenesulfonyl chloride (0.86 ml, 6.71 mmol), stirred at room temperature for 18 hr, quenched with water and diluted with ethyl acetate. The phases are separated and the organic phase is washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 3/7) to give the desired product as a white solid, 1.75 g (93%), mp 102-104° C., identified by NMR and mass spectral analyses.

Aufarbeitung

  1. stirringstirred at room temperature for 18 hr
  2. customquenched with water
  3. additiondiluted with ethyl acetate
  4. customThe phases are separated
  5. washthe organic phase is washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 3/7)

Quellen und Nachweise

ORD-Eintrag
ord-1416bd83d8b646eaba27d813b8bfc690
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919354B2

Notizen zur Reaktion

Wird geladen…