Sodium Thiosulfate → 3-Amino-5-hydroxy-4-iodobenzoic acid

HRID 1990829

Reaktionsgleichung

Reaktionsgleichung von HRID 1990829
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[I:12]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[C:10]=1[I:12])[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 1271153-Amino-5-hydroxybenzoic acid

Produkt 1

HCID 684584523-Amino-5-hydroxy-4-iodobenzoic acidAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 3-amino-5-hydroxy-benzoic acid (0.33 g, 2.16 mmol, 1.0 equiv; [CAS RN 76045-71-1]) in methanol (18 mL) at 0° C. was added within 10 min N-iodo succinimide (0.58 g, 2.59 mmol, 1.2 equiv), dissolved in methanol (3 mL). After stirring for 15 min, the reaction mixture was poured on ice and partly decolorized by addition of a 5% solution of sodium thiosulfate. The solution was extracted with ethyl acetate (3×50 mL), the combined organic phases dried over MgSO4, concentrated by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with ethyl acetate/methanol (9:1) providing 0.21 g (35%) of the title compound. 1H NMR (300 MHz, DMSO): δ 5.25 (br s, 2H), 6.61 (d, J=1.9 Hz, 1H), 6.78 (d, J=1.9 Hz, 1H), 10.16 (br s, 1H), 12.58 (br s, 1H). MS (ISP): 280.0 [M+H]+.

Aufarbeitung

  1. additionthe reaction mixture was poured on ice
  2. extractionThe solution was extracted with ethyl acetate (3×50 mL)
  3. dry with materialthe combined organic phases dried over MgSO4
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customthe crude material purified with column chromatography on silica eluting with ethyl acetate/methanol (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-e4ae248150f44f4dac2f170f0921f108
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645753B2

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