Triethylamine → 5-[(2-Chloroethyl)carbamoyloxy]-1,3-benzoxathiol-2-one

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Reaction Steps

5-hydroxy-1,3-benzoxathiol-2-one (14.0 grams) was mixed with 2-chloroethyl isocyanate (8.79 grams) in 170 milliliters of methyl ethyl ketone in the presence of 0.84 gram of triethylamine. The resulting mixture was heated at reflux temperature with stirring for 6 hours and 20 minutes. The solvent was then removed by evaporation in vacuo. The residue was recrystallized from carbon tetrachloride (containing a small amount of ethyl acetate). A subsequent recrystallization from toluene gave the purified product, 5-[(2-chloroethyl)carbamoyloxy]-1,3-benzoxathiol-2-one, as a white crystal line solid with a melting point of 105.5°-107.5° C. Elemental analysis calculated for C10H8ClNO4S (percent): carbon--43.88; hydrogen--2.95; nitrogen--5.12. Found: carbon--43.7; hydrogen--3.13; nitrogen--5.37.

Provenance & Evidence