Réaction #61000

Équation de réaction

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

morpholine

potassium carbonate

→

title compound

Rendement 10.1%

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

Rendement 10.1%

Solvants

pentanol

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated to 100° C
2. 2
   workup.STIRRINGstirred for 40 minutes
3. 3
   AutreThe solvent was evaporated
4. 4
   ExtractionThe aqueous layer was extracted twice with ethylacetate
5. 5
   Séchagedried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Autrethe solvent was removed in vacuo
8. 8
   AutreThe crude oil was chromatographed over silicagel

Mode opératoire

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%)

Source