The Reaction of o-Aminobenzenesulfonamide with Phthalic Anhydride

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  • Imai Yoshio
    Department of Polymer Chemistry, Faculty of Engineering, Yamagata University
  • Koga Hiroshi
    Department of Polymer Chemistry, Faculty of Engineering, Yamagata University
  • Takizawa Shinichi
    Department of Polymer Chemistry, Faculty of Engineering, Yamagata University

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Other Title
  • o-アミノベンゼンスルホンアミドと無水フタル酸の反応

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Description

The formation of 11-oxo-11 H-isoindolo[1, 2-c][1, 2, 4]benzothiadiazine 5, 5-dioxide. (6)rst from o-aminobenzeResulsonamide (1) and phthalic anhydride (2) was investigated, The reaction intermediate of 2-sulfamoylphthalanilic acid (3) was synthesized by the ringwgpening addition of (1) with (2) at roointemperature. The thermal cyclodehydration of (3-) g-a. v. e (6) via the f oi ihe second inte-rmediate of N-(o-sulfamoylphenyl)-pbthajimidg (4)e Thre cyclodehydration of (3) with acetic anhydride at room temperature afforded (), whe. reAaS that vGith thi6nyl chloride- yrielded a mixturerof (4) and (6). The third intermedia-te -of-3(o-carbokyphenS1)-1, 2, 4-behzothiadiazine 1, 1-dioxide (5) was obtained by th cyclodghyd. ratign 6rmf (3) ifi hot aqu e6us sodium hydroxidb, whereas (6) was obtained by the rJeaction in the pres of a basic catalyst, such as r-piceline and tri-n-butylamine, at an elevated temperature, A probable reaction pathway was discussed.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1973 (8), 1515-1519, 1973-08-10

    The Chemical Society of Japan

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