Water → HCID 22758373, Verbindung

HRID 616308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 616308
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[S:16](=[O:18])(=[O:17])[CH2:15][CH2:14][CH2:13][S:12]2(=[O:20])=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[CH2:23]([CH:25]1[O:27][CH2:26]1)Cl.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:23][CH:25]3[O:27][CH2:26]3)[S:12](=[O:19])(=[O:20])[CH2:13][CH2:14][CH2:15][S:16]2(=[O:17])=[O:18])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 926242-(3,4-Dimethoxyphenyl)-1,3-dithiane 1,1,3,3-tetraoxide

Produkt 1

HCID 22758373HCID 22758373, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

9.6 g of 2-(3,4-dimethoxyphenyl)-m-dithiane-1,1,3,3-tetraoxide (prepared as described in Example 2) are dissolved in 35 ml of dimethylformamide and, with stirring under argon, treated with 1.2 g of sodium hydride at room temperature. The suspension is stirred at 40° C for a further 0.5 hour, then cooled and treated with 2.8 g of epichlorohydrin. The mixture is then heated at 100° C for 16 hours. After cooling to room temperature, the suspension is poured on to water and the oily material extracted with chloroform. After evaporation of the solvent, the residue is chromatographed on silica gel with chloroform/ethanol (98:2). The 2-(3,4-dimethoxyphenyl)-2-(2,3-epoxypropyl)-m-dithiane-1,1,3,3-tetraoxide obtained is recrystallized from methylene chloride/ethanol and has a melting point of 175°-176° C.

Aufarbeitung

  1. stirringThe suspension is stirred at 40° C for a further 0.5 hour
  2. temperaturecooled
  3. temperatureAfter cooling to room temperature
  4. extractionthe oily material extracted with chloroform
  5. customAfter evaporation of the solvent
  6. customthe residue is chromatographed on silica gel with chloroform/ethanol (98:2)

Quellen und Nachweise

ORD-Eintrag
ord-950013ef2b524584bc0a8147d16f5ab4
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04073797

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