Toluene → Benzamide, thio-3,4,5-trimethoxy-

HRID 992983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992983
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([NH2:8])=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:25]2)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](=[S:25])[NH2:8]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 183343,4,5-TrimethoxybenzamideHCID 87949Lawesson's reagent

Produkt 1

HCID 3033195Benzamide, thio-3,4,5-trimethoxy-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3,4,5-Trimethoxybenzamide (5.0 g) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (5.24 g) were added to toluene, and the mixture was stirred at 70° C. After 5 hours, the reaction mixture was cooled back to room temperature, diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to 1:2) to obtain yellow crystals, and the crystals were further recrystallized from ethyl acetate-hexane to obtain the title compound.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled back to room temperature
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to 1:2)
  6. customto obtain yellow crystals
  7. customthe crystals were further recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-be5153d391294b19856519af253a945d
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06472386B1

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