Ethyl Acetate → HCID 68884629, compound

Participants

Reaction Steps

A flame-dried flask was charged with chlorosulfonyl isocyanate. Anhydrous formic acid (96%) was added dropwise resulting in evolution of a gas. The solution solidified halfway through the addition of the formic acid and eventually turned to a cloudy liquid (the crude sulfamyl chloride). The solution was stirred at room temperature until no further gas evolution was observed. The sulfonyl chloride was diluted with 20 mL dry methylene chloride and added to a 0° C. solution of 101/triethyl amine in 20 mL methylene chloride. The reaction was stirred from 0° C. to room temperature over 2 hours (TLC showed approximately 50% starting material in 30% ethyl acetate/hexanes) and overnight at room temperature. The reaction showed mostly two spots by TLC (70:30 ethyl acetate:hexanes). The reaction was diluted with methylene chloride, washed with 10% HCl, dried over sodium sulfate, filtered, and concentrated to a light yellow oil. The crude mixture was purified by flash column by adsorbing onto silica and eluting with 20% ethyl acetate/hexanes to recover starting material and the white solid 102.

Provenance & Evidence