Chlorosulfonyl isocyanate → HCID 10535719, compound

Participants

Reaction Steps

A solution of chlorosulfonyl isocyanate in toluene was added to a solution of 2-hydroxy-2-methyl propiophenone in anhydrous toluene at 0° C. The mixture was stirred at room temperature for 1.5 hours then the resulting precipitate was collected. The precipitate was taken up in dioxane, cooled to 0°, then triturated with water. Prior to extraction with ether the dioxane solution was stirred overnight at room temperature. Extracted ether phase was treated with aqueous sodium bicarbonate until neutral, dried over sodium sulfate, and concentrated to leave a clear colorless oil. Upon trituration with petroleum ether the oil crystallized to leave a white solid. After drying the solid, 2-carbamoyl-2-methyl propiophenone was obtained in 60% yield. This carbamate was heated at 180° C. under a weak vacuum to form the imine. The carbamate melted at 120° C., was stirred at 180° C. for 30-50 minutes, then solidified upon cooling. The crude product was recrystallized from benzene/cyclohexane to give a 73% yield of the desired product with mp. 106°-108.5° C. (lit. 111-111.5). The product was confirmed by NMR, MS, and IR analysis. ##STR15##

Provenance & Evidence