Sodium Sulfate → HCID 59421275, Verbindung

HRID 883004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883004
[O-:1]S([O-])(=O)=O.[Na+].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:19]([O:21][C:22]([C:24]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[N:26][C:27]([S:30][CH3:31])=[N:28][CH:29]=1)=[O:23])[CH3:20].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:19]([O:21][C:22]([C:24]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[N:26][C:27]([S:30]([CH3:31])=[O:1])=[N:28][CH:29]=1)=[O:23])[CH3:20]

Komponenten

6

Edukt 4

HCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59421256Ethyl 4-(2-fluorophenyl)-2-(methylthio)-5-pyrimidinecarboxylate

Produkt 1

HCID 59421275HCID 59421275, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A Na2SO4-dried solution of m-CPBA (10.64 g, ca. 45 mmol) in CH2Cl2 (100 mL) was added drop wise to a cold (−65° C.) solution of 4-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester in CH2Cl2 (200 mL) keeping the temperature below −65° C. The yellow suspension was allowed to warm to 0° C. over 1 hour. After 3 hours at 0° C., a saturated aqueous NaHCO3 solution (100 mL) was added to quench the reaction. The organic layer was separated, washed with saturated aqueous NaCl solution, dried over Na2SO4, and concentrated. The product was taken up in CH2Cl2 and washed again with a saturated aqueous NaHCO3 solution to remove traces of m-C(P)BA giving 4-(2-fluoro-phenyl)-2-methanesulfinyl-pyrimidine-5-carboxylic acid ethyl ester (12.86 g, >100%).

Aufarbeitung

  1. customthe temperature below −65° C
  2. customto quench
  3. customthe reaction
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaCl solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. washwashed again with a saturated aqueous NaHCO3 solution
  9. customto remove traces

Quellen und Nachweise

ORD-Eintrag
ord-f1658885cabb45a3bf6878a5a5ba096e
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236815B2

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