Sodium 3-nitrobenzenesulfonate → N,N-Dimethyl-N-(2-benzoylaminoethyl)benzylammonium m-Nitrobenzenesulfonate

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Reaction Steps

A solution of 11.26 grams (0.05 mol) of sodium m-nitrobenzenesulfonate in 50 milliters of water was added to a solution of 15.94 grams (0.05 mol) of the N,N-dimethyl-N-(2-benzoylaminoethyl)benzylammonium chloride, prepared as described in Example 2, in 50 milliters of water. An oily precipitate formed. The water layer was decanted and the oil was rinsed with water, dissolved in methylene chloride, dried over magnesium sulfate and concentrated to a viscous oil. The oil was treated with ligroine (bp=35°-60° C.) with warming. The oil crystallized and the solid formed was collected and recrystallized from isopropanol. The yield of product was 10.75 grams (44.28% of theory); mp=109°-112° C.

Provenance & Evidence