Pyridine → HCID 178444378, compound

Participants

Reaction Conditions

Reaction Steps

7.2 Ml. of benzenesulfonyl chloride are added dropwise while stirring to a suspension of 13.2 g. of crude trans-4-[5-(trans-4-n-pentylcyclohexyl)-2-pyrimidinyl]cyclohexane carboxamide in 150 ml. of pyridine. The mixture is then warmed to 55° C. for 3 hours in an oil-bath. The mixture is poured into 500 ml. of ice-water and the product is taken up in methylene chloride. The extract is washed successively with 3-N hydrochloric acid, saturated sodium bicarbonate solution and water, dried over sodium sulfate and evaporated. The crude product is chromatographed on a column of 500 g. of silica gel with toluene/5% acetone (v/v). The first fractions are mixtures and are discarded. The later fractions, which are uniform according to thin-layer chromatography, are dissolved in hexane, filtered hot with active carbon and recrystallized from the filtrate. There is obtained pure trans-4-[5-(trans-4-n-pentylcyclohexyl)-2-pyrimidinyl]cyclohexane carbonitrile; melting point 109.5° C., clearing point 175° C.

Provenance & Evidence