Ammonia → Thiourea, beta-D-glucopyranosyl-

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Reaction Steps

N-(2,3,4,6-Tetra-O-acetyl-β-D glucopyranosyl)-5-benzylidenerhodanine(5.52 g., 0.01 mole) was added to a solution of 50 ml. of methanol saturated with ammonia at 0° in a pressure bottle. The mixture was stirred at room temperature for 18 hours with the stopper well closed. The mixture was evaporated to a syrupy material below 30° in vacuo. The residue was dissolved in the minimum amount of methanol and passed through a silica gel column(2.54×15 cm) with aid of additional methanol. One hundred ml. of effluent was collected and concentrated. During the concentration, a precipitate was formed. The white precipitate was filtered and dried at room temperature in vacuo, yielding 2.04 g. (86.8%); m.p. 207°-209°(dec.). (Lit. m.p. 207°-210°(83), m.p. 211°-212°(32), m.p. 205°-207°(86).

Provenance & Evidence