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

HRID 1927144노트

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HRID 1927144 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 597652461-amino-5-(3-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione수율 53.2%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-270d63b5761b4f2788cffb7616eb366c
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183260B2

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