Sodium Iodide → N-Methyl-N-(5-nitrobenzofur-2-ylmethyl)-4-nitrophenethylamine

HRID 467091

Reaktionsgleichung

Reaktionsgleichung von HRID 467091
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.Br[CH2:15][C:16]1[O:17][C:18]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:19]=2[CH:20]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[CH2:15][C:16]1[O:17][C:18]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:19]=2[CH:20]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2794239N-methyl-4-nitrophenethylamineHCID 114141792-(Bromomethyl)-5-nitro-1-benzofuran

Produkt 1

HCID 15735404N-Methyl-N-(5-nitrobenzofur-2-ylmethyl)-4-nitrophenethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-Methyl-4-nitrophenethylamine (0.41 g, 2.3 mmole), 2-bromomethyl-5-nitrobenzofuran (0.66 g, 2.6 mmole), sodium iodide (0.39 g, 2.6 mmole) and potassium carbonate (0.36 g, 2.6 mmole) were heated at reflux temperature in acetonitrile (50 ml) for 8 days. The solvent was then evaporated, water was added, and the mixture extracted three times with methylene chloride. The combined organic extracts were washed with water, dried (MgSO4) and evaporated to give a semi-solid which was recrystallised from isopropanol to give the title compound, yield 380 mg.

Aufarbeitung

  1. customThe solvent was then evaporated
  2. additionwater was added
  3. extractionthe mixture extracted three times with methylene chloride
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a semi-solid which
  8. customwas recrystallised from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-ad3a2c54629f43b28311db2f18ad79eb
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158964

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