Water → 2-(4-methylphenyl)sulfonyl-N-(2-sulfoethyl)acetamide

HRID 433051

Reaktionsgleichung

Reaktionsgleichung von HRID 433051
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.[Li].[S:12]([CH2:16][CH2:17][NH:18][C:19](=[O:22])[CH2:20]Br)([OH:15])(=[O:14])=[O:13].O>C(O)C>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([S:7]([CH2:20][C:19]([NH:18][CH2:17][CH2:16][S:12]([OH:15])(=[O:14])=[O:13])=[O:22])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10818p-Toluenesulfinic acidHCID 3028194Lithium4×HCID 19908000N-(2-sulfoethyl)-2-bromoacetamide

Produkt 1

HCID 223236362-(4-methylphenyl)sulfonyl-N-(2-sulfoethyl)acetamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 5-liter flask equipped with a mechanical stirrer and reflux condenser was added p-toluenesulfinic acid, lithium salt (308.57 g), N-(2-sulfoethyl)-2-bromoacetamide, lithium salt (527.39 g), water (180 ml), and ethyl alcohol (3380 ml). The resulting suspension was heated to reflux. After about an hour of reflux, nearly all of the reactants had dissolved. Reflux was continued another four hours, and the solution was filtered hot through a Celite pad to remove some haziness. The solution was cooled overnight to room temperature. The solid that formed was collected and washed with 1 liter of 95% ethyl alcohol/water. The white solid was air dried and then dried at high vacuum, providing 553.88 g (89% yield) of 2-(4-methylphenyl)sulfonyl-N-(2-sulfoethyl)acetamide, lithium salt (Intermediate 1). HPLC analysis showed no detectable impurities. Ion chromatography indicated 0.035 weight % bromide and 1.8 weight % lithium. The material exhibited an acceptable proton spectrum.

Aufarbeitung

  1. customTo a 5-liter flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe resulting suspension was heated to reflux
  4. temperatureAfter about an hour of reflux
  5. dissolutionnearly all of the reactants had dissolved
  6. temperatureReflux
  7. filtrationthe solution was filtered hot through a Celite pad
  8. customto remove some haziness
  9. temperatureThe solution was cooled overnight to room temperature
  10. customThe solid that formed
  11. customwas collected
  12. washwashed with 1 liter of 95% ethyl alcohol/water
  13. customdried
  14. customdried at high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9b3d21d3d22e4b0aa3bf7311c8faaa25
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667148B1

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