Methyl iodide → 2-Methyl-1,2-benzoisothiazolin-3-one

Participants

Reaction Steps

To a stirred suspension of 1,2-benzisothiazolin-3-one lithium salt in THF (3 ml per gram of BIT salt) was added methyl iodide (1.1 molar equivalents). The resulting slurry was stirred at ambient temperature for 72 hours. HPLC analysis showed greater than 97% alkylation of 1,2-benzisothiazolin-3-one lithium salt. The mixture was allowed to cool and the crude product isolated as a mixture of N-methyl-1,2-benzisothiazolin-3-one and 3-methoxy-1,2-benzisothiazolin-3-one in 98.8:1.2 ratio.

Provenance & Evidence