Thionyl Chloride → 2,4,6,7-Tetramethyl-5-nitro-2,3-dihydro-1-benzofuran-2-carbonyl chloride

HRID 1987770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987770
[CH3:1][C:2]1([C:17]([OH:19])=O)[CH2:6][CH:5]2[CH:7]([CH3:16])[C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:12])[C:10]([CH3:11])=[C:4]2[O:3]1.S(Cl)([Cl:22])=O>C(Cl)Cl>[CH3:1][C:2]1([C:17]([Cl:22])=[O:19])[CH2:6][C:5]2[C:7]([CH3:16])=[C:8]([N+:13]([O-:15])=[O:14])[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 688444542,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid

Produkt 1

HCID 231183052,4,6,7-Tetramethyl-5-nitro-2,3-dihydro-1-benzofuran-2-carbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.5 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid, 20 ml of methylene chloride and 0.27 g of thionyl chloride were added, followed by heating at reflux for 2 hours. After returning the temperature to room temperature, the solvent was distilled off to obtain 2,4,6,7-tetramethyl-5-nitro-2,3-dihydrobenzofuran-2-carbonyl chloride. To 0.33 g of 2,3,4,9-tetrahydro-1H-beta-carboline, 0.23 g of triethylamine and 15 ml of DMF, a solution prepared by dissolving 2,4,6,7-tetramethyl-5-nitro-2,3-dihydrobenzofuran-2-carbonyl chloride in DMF was added, followed by stirring overnight at room temperature. The mixture was poured into ice-water and a crystal was collected by filtration. The crystal was dissolved in chloroform, washed with saturated saline and dried over anhydrous magnesium sulfate and, after the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain 0.54 g of the objective product.

Aufarbeitung

  1. temperatureby heating
  2. temperatureat reflux for 2 hours
  3. customto room temperature
  4. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-8d78fc8075284507873cff506f4e39ce
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553837B2

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