Asymmetric Synthesis of Modafinil and its Derivatives by using the Functionalized Silica-based Mesoporous MCM-41

Document Type: Research Paper

Author

Abstract

Modafinil [2-[(diphenylmethyl)sulfinyl]acetamide] is used clinically in the treatment of
narcolepsy and sleeping disorders. The synthesis of modafinil, begins with the reaction of
benzhydrol and thioglycolic acid in trifluoroacetic acid to afford benzhydrylsulfinyl acetic
acid. The reaction of acid with thionyl chloride in benzene followed by treatment with
ammonium hydroxide gave acetamide. Synthesis of novel heterogeneous chiral catalyst
by a simple and efficient method has been reported. The first, a new derivative of chiral
ligand (containing amine group) in 6 steps from a cheap and readily available substrate
(4-aminobenzoic acid) were synthesized in good yield. Then, this chiral ligand immobilized
on silica-based mesoporous MCM-41 through its amine group. The obtained catalysts were
characterized with FT-IR, XRD, BET, SEM, IR, 1H NMR,13C NMR and mass spectral and
used for the first time in oxidation of benzhydrylsulfinyl acetic acid and its derivatives. The
reaction using this catalysts exhibits very good yield.

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