The Reaction of N-(Phenylsulfonyl)phthaiimide and N-Mesylphthalimide with Various Amines

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  • Imai Yoshio
    Department of Polymer Chemistry, Faculty of Engineering, Yamagata University
  • Ishimori Motokazu
    Department of Polymer Chemistry, Faculty of Engineering, Yamagata University

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Other Title
  • N-(フェニルスルホニル)フタルイミドおよびN-メシルフタルイミドとアミン類の反応

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Description

The formation of N-substituted phthalimides by the reaction of N-(phenylsulfonyl)phthalimide (PSPI) and N-mesylphtalimide (MSPI) with various amines was investigated. The reaction of PSPI with aniline at room temperature in THF gave the ring-opening adduct, N-phenyl-N (phenylsulfonyl)-phthalamide (1a), whereas that in THF with basic catalysts or in basic solvents afforded N-phenylphthalimide (2). Similarly, N-mesyl-N -phenylphthalamide (1b)and (2) were synthesized from MSPI with aniline. The adducts (1a)and (1b) were converted by heating at 160 C into (2) by the elimination of sulfonamides. PSPI also reacted with various amines in ethanol at 80 C to form N-substituted phthalimides in good yields.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1973 (9), 1729-1733, 1973-09-10

    The Chemical Society of Japan

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