Hydrogen Sulfide → HCID 20464707, compound

Participants

Reaction Steps

Ethyl 7-chloro-4,10-dihydro-10,α-dioxo-1-methyl-1H-[1]benzothiepino[4,3-b]pyrrole-2-acetate (87 mg, 0.23 mmol) is dissolved in pyridine (2 ml) and placed in a resealable pressure tube along with imidazole (100 mg) and a small stirring bar. The tube and its contents are cooled to -78° and hydrogen sulfide (0.5 ml) is conducted inside it. The tube is then sealed and allowed to come to room temperature with stirring. The mixture is stirred for three hours, then cooled again to -78° and the tube is opened. The tube is allowed to warm and the hydrogen sulfide evaporates. When bubbling ceases, the tube contents are poured into 1.2 N aqueous HCl (30 ml), and the resulting heterogeneous mixture is extracted with ether (2×50 ml). The combined ether layers are washed with 10% aqueous sodium carbonate (3×15 ml), saturated aqueous brine (15 ml), and dried with sodium sulfate. The solvent is removed to give a white solid smelling like garlic. This material is purified by preparative TLC (1/1 EtoAc/Hex, silica gel 0.70) to give 73 mg of ethyl 7-chloro-4,10-dihydro-1-methyl-10-oxo-1H-[1]benzothiepino[4,3-b]pyrrole-2-acetate (88%).

Provenance & Evidence