Sodium Dithionite → 1-amino-5-(3-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

HRID 1927144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927144
[N+:1]([C:4]1[S:5][CH:6]=[C:7]2[C:11](=[O:12])[N:10]([C:13]3([CH3:21])[CH2:18][CH2:17][C:16](=[O:19])[NH:15][C:14]3=[O:20])[C:9](=[O:22])[C:8]=12)([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CC(C)=O.O>[NH2:1][C:4]1[S:5][CH:6]=[C:7]2[C:11](=[O:12])[N:10]([C:13]3([CH3:21])[CH2:18][CH2:17][C:16](=[O:19])[NH:15][C:14]3=[O:20])[C:9](=[O:22])[C:8]=12

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 597652841-nitro-5-(3-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

Produkt 1

HCID 597652461-amino-5-(3-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dioneAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

0.323 g of 1-nitro-5-(3-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione was dissolved in 10 mL of acetone, and a solution obtained by dissolving 0.783 g Na2S2O4 in 100 mL of water was added. The reaction mixture was refluxed for 2 h, cooled, and 100 mL of water were added. The aqueous phase was extracted with ethyl acetate (3×50 mL), the organic phases were combined and washed with 40 mL of water and 40 mL of brine, dried over anhydrous MgSO4, filtered, and evaporated to dryness. The remaining residue was purified on silica gel column chromatography to obtain a solid (0.156 g). MS (m/z): 292 (M−1)+.

Aufarbeitung

  1. customa solution obtained
  2. additionwas added
  3. temperatureThe reaction mixture was refluxed for 2 h
  4. temperaturecooled
  5. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  6. washwashed with 40 mL of water and 40 mL of brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe remaining residue was purified on silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-270d63b5761b4f2788cffb7616eb366c
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183260B2

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