Hydrogen Peroxide → 5,5-Dioxo-2-(6-methylpyridazin-3-ylamino)dibenzothiophene

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Reaction Steps

Hydrogen peroxide (100 vols, 1 ml) was added to 2-(6-methylpyridazin-3-ylamino)dibenzothiophene Example 74; 300 mgs, 1.03 mmol) in acetic acid (3 ml) and conc. sulphuric acid (0.1 ml) and the mixture was heated to 60° C. for 40 minutes. On cooling to room temperature the mixture was diluted with DCM:MeOH (1:19) washed with aqueous potassium carbonate, dried over sodium sulphate and concentrated. Chromatography (eluent gradient of DCM to DCM:MeOH (1:1)) gave the product as an off white solid (0.131 g). NMR: 9.87 (brs, 1H), 8.48 (brs, 1H), 8.00-7.70 (m, 5H), 7.65 (t, 1H), 7.45 (d, 1H), 7.20 (d, 1H), 2.52 (s, 3H); m/z 324.28.

Provenance & Evidence