Iodoethane → HCID 66720186, Verbindung

HRID 348519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348519
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=3)=[O:5])[CH3:2].[H-].[Na+].[CH2:23](I)[CH3:24]>CN(C=O)C.[NH4+].[Cl-].O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH2:23][CH3:24])[C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Komponenten

7

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 66720295Ethyl 6-methoxy-9H-carbazole-3-carboxylate

Produkt 1

HCID 66720186HCID 66720186, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A solution of 6-methoxycarbazole-3-carboxylic acid ethyl ester (1.28 g, 4.77 mmol) in DMF (8 mL) was added to a suspension of sodium hydride (60% in mineral oil, 0.286 mg, 7.15 mmol) in DMF at 0° C. The reaction was stirred for 30 minutes then ethyl iodide was added (0.89 g, 5.72 mmol). The reaction was allowed to reach room temperature and was stirred for further 15 hours then was diluted with NH4Cl sat. and water. The reaction was extracted with tert-butylmethyl ether and the organic phase was washed with water then brine. The organic layer was dried over sodium sulfate and the solvent concentrated in vacuo to give a crude which was purified by column (10% ethyl acetate/hexane) to afford 0.79 g of the title compound.

Aufarbeitung

  1. customto reach room temperature
  2. stirringwas stirred for further 15 hours
  3. extractionThe reaction was extracted with tert-butylmethyl ether
  4. washthe organic phase was washed with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationthe solvent concentrated in vacuo
  7. customto give a crude which
  8. customwas purified by column (10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-527c9943c4d04d53b07c1f3a6cb9adcc
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176322B2

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