Carbon Disulfide → 2-Thioadenosine

Participants

Reaction Steps

0.45 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide O-(p-methylbenzyl)-oxime was dissolved in a mixture of 0.30g of sodium hydroxide, 5 ml of methanol and 0.5 ml of carbon disulfide, and the resulting mixture was allowed to react in an autoclave at 130° C for 4 hours under autogenous pressure (about 10 Kg/cm2). The reaction mixture was concentrated to dryness, and the residue was dissolved in water. The resulting aqueous solution was adjusted to a pH of 2 with hydrochloric acid, and the precipitated crystals were filtered to obtain crude 2-thioadenosine. The crude product was dissolved in aqueous ammonia, filtered and adjusted to a pH of 2 with hydrochloric acid to obtain 0.27 g of pure 2-thioadenosine having a melting point of 198° C (with decomposition) in a 72% yield.

Provenance & Evidence