2-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine → 3,4-Diethoxycarbonyl-5-nitro-6-phenyl-2-(p-tolylsulfonyl)pyridine

HRID 37505

Reaktionsgleichung

Reaktionsgleichung von HRID 37505
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-:20])=[O:19])=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:3]=1.O.O.O.O.[C:31]1([CH3:40])[CH:36]=[CH:35][C:34]([S:37]([O-:39])=[O:38])=[CH:33][CH:32]=1.[Na+]>C(O)C>[CH2:11]([O:10][C:8]([C:7]1[C:2]([S:37]([C:34]2[CH:35]=[CH:36][C:31]([CH3:40])=[CH:32][CH:33]=2)(=[O:39])=[O:38])=[N:3][C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:5]([N+:18]([O-:20])=[O:19])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH3:12]

Komponenten

4

Edukt 2

HCID 199355872-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridineHCID 23690860Sodium 4-methylbenzene-1-sulfinate--water (1/1/4)

Produkt 1

HCID 199356083,4-Diethoxycarbonyl-5-nitro-6-phenyl-2-(p-tolylsulfonyl)pyridineAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 0.379 g of 2-chloro-3,4- diethoxycarbonyl-5-nitro-6-phenylpyridine, 0.5 g of sodium p-toluenesulfinate tetrahydrate and 15 ml of ethanol was heated under reflux for 3 hours. After concentration, the concentrate was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. After the solvent was distilled off, the residue was subjected to silica gel column chromatography with n-hexane/ethyl acetate (4:1) as the eluent. The eluate was concentrated to give crystals. The obtained crystals were recrystallized from the same solvent, to give 0.289 g of the title compound as colorless needles.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationAfter concentration
  4. extractionthe concentrate was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationAfter the solvent was distilled off
  8. concentrationThe eluate was concentrated
  9. customto give crystals
  10. customThe obtained crystals were recrystallized from the same solvent

Quellen und Nachweise

ORD-Eintrag
ord-e8df5648462847aea31600732ea0cdf2
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420275

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