Iodoethane → 3-Amino-5-ethoxy-4-iodo-benzoic acid methyl ester

HRID 502367

Reaktionsgleichung

Reaktionsgleichung von HRID 502367
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([I:11])=[C:6]([NH2:12])[CH:5]=1.[CH2:14](I)[CH3:15].CC(C)([O-])C.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH2:14][CH3:15])[C:7]([I:11])=[C:6]([NH2:12])[CH:5]=1

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 23676156Sodium t-butoxideHCID 68458438Methyl 3-amino-5-hydroxy-4-iodobenzoate

Produkt 1

HCID 684595793-Amino-5-ethoxy-4-iodo-benzoic acid methyl esterAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-5-hydroxy-4-iodo-benzoic acid methyl ester (0.25 g, 0.85 mmol) in DMF (3 mL) and ethyl iodide (0.10 mL, 0.146 g, 0.94 mmol) at 0° C. was added sodium tert-butoxide (0.11 g, 0.94 mmol) in small portions over a time period of 10 min. After stirring for 1 h, the cooling bath was removed and the reaction mixture stirred at rt for an additional 18 h. The solution was concentrated by evaporation under reduced pressure and extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over MgSO4, concentrated by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1) yielding 0.19 g (69%) of the title compound.

Aufarbeitung

  1. customthe cooling bath was removed
  2. stirringthe reaction mixture stirred at rt for an additional 18 h
  3. concentrationThe solution was concentrated by evaporation under reduced pressure
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ea048377ca0c478596b80b4e3e8e8be2
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772253B2

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