Reacción #61000

Ecuación de reacción

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

morpholine

potassium carbonate

→

title compound

Rendimiento 10.1%

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

Rendimiento 10.1%

Disolventes

pentanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated to 100° C
2. 2
   workup.STIRRINGstirred for 40 minutes
3. 3
   OtroThe solvent was evaporated
4. 4
   ExtracciónThe aqueous layer was extracted twice with ethylacetate
5. 5
   Secadodried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Otrothe solvent was removed in vacuo
8. 8
   OtroThe crude oil was chromatographed over silicagel

Procedimiento

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%)

Fuente