Efficient Synthesis of Thiobenzanilides by Willgerodt-Kindler Reaction with Base Catalysts

Ken Okamoto, Takakazu Yamamoto, Takaki Kanbara*

*Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), University of Tsukuba, 1-1-1 Ten-noudai, Tsukuba 305-8573, Japan, Email: kanbaraims.tsukuba.ac.jp

K. Okamoto, T. Yamamoto, T. Kanbara, Synlett, 2007, 2687-2690.

DOI: 10.1055/s-2007-991073

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Abstract

Willgerodt-Kindler reaction between anilines and aromatic aldehydes readily proceeds in the presence of a catalytic amount of Na₂S·9H₂O to give thiobenzanilides good yields. The base catalyst was also effective for the preparation of thiobenzamide using aqueous ammonia.

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Key Words

Willgerodt-Kindler Reaction, sulfur, catalysis, condensation, aromatic amines, thioamides, multicomponent reactions

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ID: J60-Y2007-3440