(Chloromethyl)sulfonyl chloride → HCID 18358029, compound

Participants

Reaction Steps

The reaction was carried out as described in Example 60, but using 3 ml of a solution of 1.6 mmol of 2-[5-(1,2-dithiolan-3-yl)pentyl]isoindoline-1,3-dione (prepared as described in Example 58) in toluene, 2 ml of methanol, 2 ml of butylamine, 5 ml of anhydrous tetrahydrofuran, 0.33 ml of triethylamine and 0.21 ml of chloromethanesulfonyl chloride. The solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 2:5 and 2:3 by volume mixtures of ethyl acetate and hexane as the eluent. The ethyl acetate was removed from the eluate solution by evaporation under reduced pressure, and the residue was dissolved in dioxane and then lyophilised, to obtain 42 mg of the title compound as a brown oil having an Rf value of 0.29 (silica gel thin layer chromatography; using a 2:5 by volume mixture of ethyl acetate and hexane as developing solvent).

Provenance & Evidence