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

HRID 1927137

Reaktionsgleichung

Reaktionsgleichung von HRID 1927137
[O:1]=[C:2]1[CH:7]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][S:15][CH:16]=[C:10]3[C:9]2=[O:17])[CH2:6][CH2:5][C:4](=[O:18])[NH:3]1.[H-].[Na+].[CH3:21]I.O>CN(C=O)C>[CH3:21][N:3]1[C:4](=[O:18])[CH2:5][CH2:6][CH:7]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][S:15][CH:16]=[C:10]3[C:9]2=[O:17])[C:2]1=[O:1]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 597652875-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

Produkt 1

HCID 597652475-(1-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.264 g of 5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione were dissolved in 10 mL anhydrous DMF, and 0.036 g of NaH (95%) were added. The reaction mixture was reacted at room temperature for 30 min, and 0.2 mL of CH3I were added. The reaction mixture was allowed to stir overnight. 100 mL of water were added, and the aqueous phase was extracted with ethyl acetate (3×30 mL). Organic phases were combined, washed with 30 mL of water and 30 mL of brine, dried over anhydrous MgSO4, filtered, and evaporated to dryness. A white solid (0.196 g) was obtained. 1H NMR (CDCl3): δ 7.91 (s, 2H), 4.93 (d, 1H, J=3 Hz), 3.22 (s, 3H), 3.04-2.94 (m, 1H), 2.83-2.71 (m, 2H), 2.11 (m, 1H); MS (m/z): 278 (M)+.

Aufarbeitung

  1. customThe reaction mixture was reacted at room temperature for 30 min
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×30 mL)
  3. washwashed with 30 mL of water and 30 mL of brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8f017c453f9b40edb3bc9b3030fbc774
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183260B2

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