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

HRID 1927137

Reaction equation

HRID 1927137 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-8f017c453f9b40edb3bc9b3030fbc774
Source dataset
uspto-grants-2012_05
Patent number
US08183260B2

Linked notes

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