Ethanol → (2,6-Diisopropyl-phenylsulfamoyl)-acetic acid ethyl ester

HRID 2255254

Reaktionsgleichung

Reaktionsgleichung von HRID 2255254
[S:1]([CH2:5][C:6]([OH:8])=[O:7])(O)(=[O:3])=[O:2].[CH3:9][CH2:10]O.O=P(Cl)(Cl)Cl.[CH:17]([C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:21]=1[NH2:22])([CH3:19])[CH3:18]>C(Cl)Cl>[CH3:29][CH:27]([C:23]1[CH:24]=[CH:25][CH:26]=[C:20]([CH:17]([CH3:19])[CH3:18])[C:21]=1[NH:22][S:1]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])=[O:2])[CH3:28]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 24813Phosphorus oxychlorideHCID 31257Sulfoacetic acidHCID 32484Diisopropylaniline

Produkt 1

HCID 44330987(2,6-Diisopropyl-phenylsulfamoyl)-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

Sulfoacetic acid (52 g, 371 mM) and EtOH (500 mL) were heated under reflux for 20 hours. The reaction mixture was cooled, and the excess ethanol was removed under vacuum to give 2 (see Chart I). A mixture of 2 (16.82 g, 100 mM) and POCl3 (30.67 g, 200 mM) was heated at 125° C. for 5 hours. The mixture was cooled and filtered, and excess POCl3 was removed to give 3 (see Chart I). Compound 3 (8.18 g, 43.83 mM) was added dropwise with stirring to a solution of 2,6-diisopropylaniline (15.54 g, 87.66 mM) in 50 mL CH2Cl2 maintained at 0° C. The mixture was stirred at room temperature for an additional 18 hours. The solvent was removed and the residue was redissolved in 100 mL ethyl acetate and washed with 1 N HCl and brine. The ethyl acetate was evaporated and the pure compound was isolated by chromatography over silica gel (EtOAc/hexane, 1:4 as eluant) as a white powder, 7.0 g (~50%), mp 114°-116° C.

Aufarbeitung

  1. temperatureunder reflux for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe excess ethanol was removed under vacuum
  4. customto give 2 (see Chart I)
  5. temperatureThe mixture was cooled
  6. filtrationfiltered
  7. customexcess POCl3 was removed
  8. customto give 3 (see Chart I)
  9. temperaturemaintained at 0° C
  10. customThe solvent was removed
  11. dissolutionthe residue was redissolved in 100 mL ethyl acetate
  12. washwashed with 1 N HCl and brine
  13. customThe ethyl acetate was evaporated
  14. customthe pure compound was isolated by chromatography over silica gel (EtOAc/hexane, 1:4 as eluant) as a white powder, 7.0 g (~50%), mp 114°-116° C.

Quellen und Nachweise

ORD-Eintrag
ord-f50c8b709851438080f600e477ebcc2b
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05239082

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