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

HRID 1927145
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1927145
[N+:1]([C:4]1[S:5][CH:6]=[C:7]2[C:11](=[O:12])[N:10]([CH:13]3[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH3:20])[C:14]3=[O:21])[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]([CH:13]3[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH3:20])[C:14]3=[O:21])[C:9](=[O:22])[C:8]=12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 59765277HCID 59765277, Verbindung

Produkt 1

HCID 597653111-amino-5-(1-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dioneAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

0.097 g of 1-nitro-5-(1-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 0.239 g of Na2S2O4 in 10 mL of water was added. The reaction mixture was refluxed for 2 h, cooled, and 10 mL of water were added. The aqueous phase was extracted with ethyl acetate (3×30 mL), the organic phases were combined, washed with 40 mL of water and 40 mL of brine, dried over anhydrous MgSO4, filtered, and evaporated to dryness to remove the solvent. The remaining residue was purified on silica gel column chromatography to yield a solid (0.046 g). MS (m/z): 292 (M−1)+.

Aufarbeitung

  1. customand a 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 (3×30 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. customto remove the solvent
  11. customThe remaining residue was purified on silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-31ccfa30a5ae434c86984d5f6de1dc06
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08183260B2

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