Morpholine → 5-Methylsulfanyl-2-morpholin-4-yl-benzoic acid

HRID 32722

Reaktionsgleichung

Reaktionsgleichung von HRID 32722
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCCC.[Cu]>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 6088142-Chloro-5-(methylsulfanyl)benzoic acid

Produkt 1

HCID 597935765-Methylsulfanyl-2-morpholin-4-yl-benzoic acidAusbeute 10,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 62761-PentanolLösungsmittel

Versuchsvorschrift

A mixture of 2-Chloro-5-(methylthio)-benzoic acid (1 g, 4.7 mmol), morpholine (620 ul, 7.1 mmol), potassium carbonate (1.05 g, 7.6 mmol) and Copper (24 mg, 0.38 mmol) in pentanol (6 ml) was stirred for 1 h at room temperature. The mixture was heated to 100° C and stirred for 40 minutes. The solvent was evaporated. The residue was taken up in water and acidified to pH 2. The aqueous layer was extracted twice with ethylacetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: heptane/ethylacetate 0-20% over 15 minutes to provide the title compound as a brown solid (120 mg, 10%), MS (m/e): 252.1 (M−H, 100%)

Aufarbeitung

  1. temperatureThe mixture was heated to 100° C
  2. stirringstirred for 40 minutes
  3. customThe solvent was evaporated
  4. extractionThe aqueous layer was extracted twice with ethylacetate
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe crude oil was chromatographed over silicagel

Quellen und Nachweise

ORD-Eintrag
ord-e0c7711c73034553b657b8647c7d2f47
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427612B2

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