Ammonium formate → HCID 86747129, Verbindung

HRID 266463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 266463
C([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:15][CH:16]=2)[S:9]1(=[O:11])=[O:10])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH4+:8].[CH3:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][C:14]1[CH:13]=[C:12]2[C:17]([C:18](=[O:19])[NH:8][S:9]2(=[O:11])=[O:10])=[CH:16][CH:15]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 70051691HCID 70051691, Verbindung

Produkt 1

HCID 86747129HCID 86747129, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-benzyl-6-[2-(2-methoxyethoxy)-ethoxy]saccharin (2.05 g), methanol (75-100 mL), ammonium formate (1.10 g) and palladium on carbon (10%, 1.0 g) was heated under reflux for 40 minutes, allowed to cool and filtered. The filtrate was stripped of volatiles affording 6-[2-(2-methoxyethoxy)-ethoxy]saccharin ammonium salt, a mixture of which with chloromethyl phenyl sulfide (0.79 g) and dimethylformamide was heated for eight hours at 100° C., stirred overnight at room temperature, and poured into ice-water (600 mL). The resulting mixture was extracted with dichloromethane. The dichloromethane extract was washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and stripped of dichloromethane. Column chromatography of the residue (1.70 g) on silica gel using dichloromethane-acetone (98:2) as eluant and again using dichloromethane-acetone (99:1) as eluant afforded 2-phenylthiomethyl-6-[2-(2-methoxyethoxy)-ethoxy]saccharin (0.96 g, 45% yield).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 40 minutes
  3. temperatureto cool
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-52ac9e1165114bcf9947d7665d28de89
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650422

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