Reaktion #2024594

Reaktionsgleichung

ammonium chloride

Sodium

ethylene glycol

N-[6-chloro-5-(4-methylphenyl)pyrimidin-4-yl]-4-[2-(2-tetrahydropyranyloxy)-1,1-dimethylethyl]benzenesulfonamide

→

N-[6-(2-hydroxyethoxy)-5-(4-methylphenyl)-pyrimidin-4-yl]-4-[2-(2-tetrahydropyranyloxy)-1,1-dimethyl-ethyl]benzenesulfonamide

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   Temperaturcooling
3. 3
   Extraktionthe mixture is extracted with ethyl acetate
4. 4
   WaschenThe extract is washed with a saturated aqueous sodium chloride solution
5. 5
   Trocknenthe organic layer is dried over anhydrous sodium sulfate and activated carbon
6. 6
   SonstigeThe solid materials are removed by filtration through a Celite pad
7. 7
   Einengenthe filtrate is concentrated under reduced pressure
8. 8
   SonstigeThe residue is crystallized from ethyl acetate-diisopropyl ether

Vorschrift

Sodium (35.65 g) is gradually added to ethylene glycol (1.3 liter) at 23-75° C., and thereto is added N-[6-chloro-5-(4-methylphenyl)pyrimidin-4-yl]-4-[2-(2-tetrahydropyranyloxy)-1,1-dimethylethyl]benzenesulfonamide (160 g) at 4° C. The mixture is stirred at 100° C. for 16 hours, and allowed to cool to room temperature. The reaction mixture is poured into a mixture of a saturated aqueous ammonium chloride solution and ethyl acetate under ice-cooling, and the mixture is extracted with ethyl acetate. The extract is washed with a saturated aqueous sodium chloride solution, and the organic layer is dried over anhydrous sodium sulfate and activated carbon. The solid materials are removed by filtration through a Celite pad, and the filtrate is concentrated under reduced pressure. The residue is crystallized from ethyl acetate-diisopropyl ether to give N-[6-(2-hydroxyethoxy)-5-(4-methylphenyl)-pyrimidin-4-yl]-4-[2-(2-tetrahydropyranyloxy)-1,1-dimethyl-ethyl]benzenesulfonamide (80.26 g) as colorless crystals. In addition, the mother liquor is concentrated, and the resultant is recrystallized from ethyl acetate-diisopropyl ether to give the crystals of the above compound (73.1 g).

Quelle