Sulfur Dioxide → HCID 19374697, compound

Participants

Reaction Conditions

Reaction Steps

The product from step B (0.1 g, 5.3 mmol) was dissolved in dry THF (4 mL) and cooled to -78° C. under nitrogen. n-Butyllithium (0.7 mL of a 2.5 M solution in hexanes, 1.75 mmol) was added dropwise, the mixture stirred for 1h at -78° C. A stream of sulfur dioxide gas was passed through the surface of the mixture for 15 min. and then the mixture was allowed to warm to room temperature. Evaporation of the reaction mixture provided a residue which was dissolved in water (5 mL) to which was added sodium acetate trihydrate (0.21 g, 1.39 mmol); this solution was cooled to 0° C. and hydroxylamine-O-sulfonic acid (0.18 g, 1.39 mmol) was added followed by stirring for 18 h. The reaction mixture was extracted with ethyl acetate (2×5 mL). The combined extracts were dried over MgSO4 and concentrated to a crude oil which was purified by flash column chromatography (silica, hexane-ethyl acetate gradient) to give a white solid. (0.021 g, 15%). decomposition:t>183° C. Cl-MS m/e 268 (m+H)+. 1HNMR (DMSO-d6): δ:7.90 (1H, 1s, CH); 8.22 (2H, S, NH2 exchangeable); 8.34 (1H, 1s, CH=N).

Provenance & Evidence