Water → 2-{[1-(Phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide

HRID 896290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896290
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C)C=O>[C:17]1([S:14]([N:9]2[C:10]3[C:6](=[C:5]([O:4][CH2:3][CH2:2][N:23]=[N+:24]=[N-:25])[CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 33557Sodium AzideHCID 104047244-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-Indole

Produkt 1

HCID 120184382-{[1-(Phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of 4-(2-chloroethoxy)-1-(phenylsulfonyl)-1H-indole (3.35 g, 10 mmol) and sodium azide (1.95 g, 30 mmol) in anhydrous dimethylformamide is stirred under nitrogen for 20 hr at 60° C., poured into water and extracted with diethyl ether. The extracts are combined, washed sequentially with 1N HCl, H2O and saturated NaCl, dried over MgSO4 and concentrated in vacuo to afford the title product as an off-white solid, 3.3 g (96%), identified by NMR and mass spectral analyses.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washwashed sequentially with 1N HCl, H2O and saturated NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cac6aa42a99f49cb8c930d0b249e1c97
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919354B2

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