Hydrochloric Acid → HCID 13851236, compound

Participants

Reaction Steps

5-(5-oxohexyl)thiophene-2-sulfonamide (1.7 g) was dissolved in ethanol and 0.2 grams of sodium borohydride added. After 1 hour of stirring the reaction mixture was made acidic with 1N hydrochloric acid then concentrated under vacuum. This residue was treated with 1N hydrochloric acid to insure that no borate esters were present. The product was then extracted into ether, dried over sodium sulfate and concentrated under vacuum to give 1.3 grams of an oil plus solid mixture. This was chromatographed twice using 230-400 mesh gel and eluting with 0-10% methanol in chloroform providing 0.6 g of product which was recrystallized from water. m.p. 75°-76° C. N.M.R. (CDCl3)δ1.16 (d, 3H), 1.43 (m, 5H), 1.64 (m, 2H), 2.80 (t, 2H), 3.76 (m, 1H), 5.04 (bs, 2H), 6.69 (d, 1H), 7.42 (d, 1H), Analysis calculated for C10H 17 NO3S2 : C, 45.60%; N, 5.32%; H, 6.51% and found: C, 45.41%; N, 5.53%; H, 6.63%.

Provenance & Evidence