Lithium Chloride → Ethyl[2-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate

HRID 733370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733370
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:31]C)=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][C:16]=2[O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:11])=[O:10])[CH:8]=1)#[N:2].[Cl-].[Li+]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:31])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][C:16]=2[O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 433294Lithium ChlorideHCID 17856206Ethyl[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate

Produkt 1

HCID 17856212Ethyl[2-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetateAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 148 mg of ethyl [2-[2-(5-cyano-2-methoxy-benzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate in 3 mL of N,N-dimethylformamide was added 41 mg of lithium chloride, and the mixture was stirred at 140° C. for 3 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue was added aqueous 10% citric acid solution to adjust pH4, and the mixture was extracted with 100 mL of ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 139 mg of ethyl [2-[2-(5-cyano-2-hydroxybenzenesulfonylamino)-ethyl]-5-isopropylphenoxy]acetate.

Aufarbeitung

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added aqueous 10% citric acid solution
  4. extractionthe mixture was extracted with 100 mL of ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eb9cd44af2cf412c92dceb833b7d4842
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589126B2

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