Acetic Acid → HCID 18314476, Verbindung

HRID 277382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277382
[CH3:1][C:2]([CH3:20])([C:8]1[C:12]2[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O)(=O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)Cl.[Fe]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]2[S:10][N:9]=[C:8]([C:2]([CH3:20])([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:12]=2[CH:13]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8857Ethyl Acetate2×HCID 516892Sodium BicarbonateHCID 18314471HCID 18314471, Verbindung

Produkt 1

HCID 18314476HCID 18314476, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
56 °C

Versuchsvorschrift

A mixture of ethyl α,α-dimethyl-5-nitro-1,2-benzisothiazole-3-acetate (0.714 g, 2.42 mmol), iron powder (0.500 g), 10% acetic acid (23.0 mL) and ethyl acetate (23.0 mL) is stirred at 54-58° C. for one hour, cooled, and poured into saturated sodium hydrogen carbonate solution. The resultant aqueous mixture is extracted with ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a yellow oil. Column chromatography of the oil using silica gel and a 10% ethyl acetate in methylene chloride solution gives the title product as a light brown oil which is identified by NMR spectral analysis.

Aufarbeitung

  1. temperaturecooled
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. washThe combined organic extracts are washed sequentially with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-07cd69a3d3a345deb2c75ffbc99b0f26
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355796B1

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