Water → 4-(Morpholine-4-sulfonyl)benzoic acid

HRID 1063076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1063076
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.O>C1COCC1>[N:14]1([S:2]([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)(=[O:4])=[O:3])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8083MorpholineHCID 823854-(Chlorosulfonyl)benzoic acid

Produkt 1

HCID 5594164-(Morpholine-4-sulfonyl)benzoic acidAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(chlorosulfonyl)-benzoic acid (0.5 g, 2.2 mmol) in THF (20 ml) was added morpholine (0.434 ml, 5 mmol) dropwise over 5 min, and this mixture stirred at r.t. for 1 h. Water (50 ml) was then addedand the mixture agitated, the phases were separated and the aqueous phase extracted with EtOAc (2×50 ml). The combined organic phases were washed with satd. aq. NaCl solution, dried, filtered and evaporated. The residue was chromatographed over SiO2 (Merck 230-400 mesh) eluting with a CHCl3/(acetone+10% HCO2H) (9:1), the product fractions were pooled, evaporated and dried in vacuo (0.05 mmHg, 50° C.) to afford the title compound as a beige solid (270 mg, 20% yield), MS: m/e=271 (M+).

Aufarbeitung

  1. stirringthe mixture agitated
  2. customthe phases were separated
  3. extractionthe aqueous phase extracted with EtOAc (2×50 ml)
  4. washThe combined organic phases were washed with satd
  5. dry with materialaq. NaCl solution, dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed over SiO2 (Merck 230-400 mesh)
  9. washeluting with a CHCl3/(acetone+10% HCO2H) (9:1)
  10. customevaporated
  11. customdried in vacuo (0.05 mmHg, 50° C.)

Quellen und Nachweise

ORD-Eintrag
ord-f4722d257e584980ae6e4921f9f8719f
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06963000B2

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