Hydrogen Sulfide → HCID 3006458, compound

Participants

Reaction Conditions

Reaction Steps

Dry H2S was passed through a NaOCH3 solution (1 M) (6 mL) with magnetic stirring and cooling at 0° C. for 10 minutes. Compound 18a (0.13 g; 0.5 mmole) was then added in one portion to the stirred solution of NaSH which had been generated in situ as described above. The mixture was stirred at room temperature for 4 hours and then allowed to stand at 0° C. for an additional 12 hours. The mixture was filtered and the filtrate conc. in vacuo. The residue was purified by a column (2×40 cm; prepacked in CH2Cl2) of silica gel (20 g; 70-230 mesh). Elution of the column with CH2Cl2 :CH3OH (94:6) gave the title compound, which was crystallized from H2O to afford pure 10 (0.04 g; yield 28%); m p. 180°-181° C.; IR (KBr) γ3400 and 3180 (NH2, OH), 1640 cm-1 ; UVλmax nm: (pH 1), 241 (2750) 301 (1220), MeOH, 283 (5387), pH 11, 216 (26200) 278 (5806); 1H NMR (DMSO-d6): δ3.3-3.45 (m, 4H, H-3', H-4'), 3.60 (m, 1H, H-4'), 4.62 (t, 2H, OH), 5.65 (s, 2H, H-1'), 7.9 (s, 1H, C6 --H), 7.98 (brs, 2H, D2O exchangeable, NH2), 8.15 (s, 1H, C2 --H), 9.45 and 9.60 (brs, 1 each, D2O exchangeable, CSNH2). Anal. (C11H15N5O3S·H2O). (C,H,N).

Provenance & Evidence