Sematilide can be synthesized from
benzocaine (
1). Reaction with
mesyl chloride, followed by saponification and removal of the water from the reaction mixture, gives sodium 4-[(methylsulfonyl)amino]benzoate (
2). Chlorination with
thionyl chloride gives 4-[(methylsulfonyl)amino]benzoyl chloride. Amide formation with
N,
N-diethylethylenediamine (
3) then concludes the synthesis of sematilide (
4). ==References==