Hydrochloric Acid → HCID 178459233, compound

Participants

Reaction Conditions

Reaction Steps

9.2 Ml. of benzenesulfonyl chloride are added dropwise while stirring to a suspension of 16.0 g. of trans-p-[5-(4-n-propyloxycyclohexyl)-2-pyrimidinyl]benzamide in 170 ml. of pyridine. The mixture is then warmed to 40° C. for 15 hours in an oil-bath. The clear mixture is poured into a mixture of 200 g. of ice and 24.1 ml. of concentrated hydrochloric acid and the product is taken up in methylene chloride. The extract is washed three times with 195 ml. of 3-N hydrochloric acid each time, then with 100 ml. of saturated sodium bicarbonate solution and with water, dried over sodium sulfate and evaporated. The crude product is chromatographed on a column of 200 g. of silica gel with benzene and with benzene containing 1% and 2% acetone (v/v). The fractions which are pure according to thin-layer chromatography are recrystallized from acetone/hexane. There is obtained trans-p-[5-(4-n-propyloxycyclohexyl)-2-pyrimidinyl]benzonitrile; melting point 114.5° C., clearing point 223.5° C.

Provenance & Evidence