Phosgene → HCID 178456976、化合物

関与物質

反応条件

反応手順

Phosgene (0.416 ml, 20% in toluene) was added dropwise to a solution of N-[5-chloro-3-(isopropylthiocarbamoyl)sulfamoylthiophen-2-yl]acetamide(261 mg, 0.73 mmol) and dry triethylamine (0.209 ml, 1.5 mmol) in dry tetrahydrofuran (5 ml) with stirring at 0° C. The mixture was stirred for 1 h at 0° C., and evaporated to dryness. The residue was triturated with 10 ml of water, and the precipitate was isolated by filtration, washed with water and finally deacetylated by stirring in 2 ml of 2 N sodium hydroxide for 90 min at room temperature. The solution was acidified to pH 2 with 4 M hydrochloric acid and the precipitate was filtered off and recrystallised from ethyl acetate with decolorising charcoal affording 44 mg (21%) of the pure title compound; mp 272-274° C. (ethyl acetate); 1H-NMR (DMSO-d6): δ1.16 (d, 6H, 2×CH3), 3.85 (m, 1H NCH), 7.23 (s, 1H, H-7), 7.48 (br d, 1H, NH), 11.12 (s, 1H, NH); MS: m/e 279/281 (M+).

情報源と証拠