Reaktion #61000

Reaktionsgleichung

2-Chloro-5-(methylthio)-benzoic acid

morpholine

potassium carbonate

→

title compound

Ausbeute 10.1%

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

Ausbeute 10.1%

Lösungsmittel

pentanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated to 100° C
2. 2
   workup.STIRRINGstirred for 40 minutes
3. 3
   SonstigeThe solvent was evaporated
4. 4
   ExtraktionThe aqueous layer was extracted twice with ethylacetate
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent was removed in vacuo
8. 8
   SonstigeThe crude oil was chromatographed over silicagel

Vorschrift

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%)

Quelle