Ethylene Glycol → HCID 22461012, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence