Acetic Anhydride → 1-acetamido-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

HRID 1927142Notes

Reaction equation

HRID 1927142 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]2[C:9](=[O:10])[N:8]([CH:11]3[CH2:16][CH2:15][C:14](=[O:17])[NH:13][C:12]3=[O:18])[C:7](=[O:19])[C:6]=12.[C:20](OC(=O)C)(=[O:22])[CH3:21]>>[C:20]([NH:1][C:2]1[S:3][CH:4]=[C:5]2[C:9](=[O:10])[N:8]([CH:11]3[CH2:16][CH2:15][C:14](=[O:17])[NH:13][C:12]3=[O:18])[C:7](=[O:19])[C:6]=12)(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 597652711-amino-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

Product 1

HCID 597653081-acetamido-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

Procedure

0.084 g 1-amino-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione was dissolved in 10 mL of acetic anhydride and refluxed for 6 h. The reaction mixture was cooled and evaporated to dryness. The remaining residue was purified on silica gel column chromatography to yield a solid (0.067 g). MS (m/z): 320 (M−1)+.

Workup

  1. temperaturerefluxed for 6 h
  2. temperatureThe reaction mixture was cooled
  3. customevaporated to dryness
  4. customThe remaining residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-1954838c760849bc90945b3168603000
Source dataset
uspto-grants-2012_05
Patent number
US08183260B2

Reaction notes

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