Oxalyl chloride → HCID 9908323, compound

Participants

Reaction Steps

1-(Dibenzofuran-3-sulfonylamino)-cyclohexanecarboxylic acid (0.18 g, 0.5 mmol) was dissolved in 50 mL dichloromethane with 2 drops of dimethylformamide. Oxalyl chloride (0.08 mL, 1.0 mmol) was added, and the resulting solution was stirred for 2 hours, then concentrated in vacuo. The resulting residue was dissolved in 10 mL tetrahydrofuran, and this solution was added dropwise to a mixture of sodium bicarbonate (0.61 g, 7.2 mmol) and hydroxylamine hydrochloride (0.33 g, 4.8 mmol) in 50 mL of a tetrahydrofuran/water mixture (1:1 ratio) that had been stirring for 10 minutes at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 64 hours. The reaction was concentrated in vacuo and partitioned between 1 M HCl and dichloromethane. The aqueous layer was extracted with additional dichloromethane, followed by drying the combined organic layers over magnesium sulfate, filtration, and concentration to give 0.07 g of an off-white solid, the structure of which is shown below. The compound had a melting point of about 184-186° C. 1HNMR (CDCl3): δ7.97 (d, 1H), 7.97 (s, 1H), 7.90 (dd, 2H), 7.75 (d, 1H), 7.48 (d, 1H), 7.41 (t, 1H), 7.27 (t, 1H), 6.65 (s, 1H), 1.79 (m, 4H), 1.14 (m, 6H) ppm. Analysis showed the compound to have an empirical formula of (C19H20N2O5S.0.25H2O).

Provenance & Evidence