Dimethyl Sulfoxide → 6-[4-(2-Pyridylmercapto)-butoxy]-3,4-dihydro-carbostyril

Participants

Reaction Conditions

Reaction Steps

14.4 gm (0.13 mol) of 2-mercapto-pyridine and 17.9 gm (0.13 mol) of potassium carbonate were stirred into 360 ml of dimethylsulfoxide which had been dried over a molecular sieve, and the solution was admixed with 36 gm (0.12 mol) of 6-(4-bromo-butoxy)-3,4-dihydro-carbostyril (m.p. 142°-147° C.; prepared from 6-hydroxy-carbostyril and 1,4-dibromo-butane). The mixture was stirred for 15 hours at about 25° C., then poured into 3.6 liters of water, and the aqueous mixture was stirred for 30 minutes. The precipitate formed thereby was collected by suction filtration, thoroughly washed with water, dried and recrystallized from xylene in the presence of activated charcoal, yielding 32 gm (81.2% of theory) of a light yellow crystalline product having a melting point of 123°-124.5° C. It was identified to be the compound of the formula ##STR9##

Provenance & Evidence