N-Iodosuccinimide → Benzyl[3-(aminocarbonyl)-5-iodo-2-thienyl]carbamate

HRID 385694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385694
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:20]N1C(=O)CCC1=O>ClCCl.C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[S:12][C:13]([I:20])=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 2

HCID 120273N-Iodosuccinimide2×HCID 59525796Benzyl[3-(aminocarbonyl)-2-thienyl]carbamate

Produkt 1

HCID 59525870Benzyl[3-(aminocarbonyl)-5-iodo-2-thienyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittelHCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

To a solution of benzyl[3-(aminocarbonyl)-2-thienyl]carbamate (4.39 g, 15.88 mmol) in dichloromethane (440 mL) was added N-iodosuccinimide (3.57 g, 15.88 mmol). An additional amount of N-iodosuccinimide (1.07 g) was added in 3 portions over the next 60 min to drive the reaction to completion. The dark reaction mixture was diluted with ethyl acetate (700 mL), hexanes (100 mL), aqueous sodium thiosulfate (1 M, 150 mL), and aqueous sodium hydroxide (1 M, 300 mL). The layers were separated, and the organic layer was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (150 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound as a solid.

Aufarbeitung

  1. customthe reaction to completion
  2. customThe dark reaction mixture
  3. customThe layers were separated
  4. washthe organic layer was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (150 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dfc453da18ff48888508b1b902ef62e4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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