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■ Cycloaddition in Synthesis of Sulfonamide Derivatives. VI Unexpected Products from the Reaction of Dithiocarbamate with Chlorosulfonyl Isocyanate a Novel Synthetic Route to 5-Amino-1,2,4-dithiazol-3-one and N,N-Disubstituted N‘-Chlorosulfonylcarbamimidoyl Chloride

Tsuneo Iwakawa,* Tomohiro Sato, and Akira Murabayashi

*Aburahi Laboratories, Shionogi & Co. Ltd., Gotanda, Koka-cho, Koka-gun, Shiga 520-3423, Japan

Abstract

Reaction of propyl N-methyl-N-phenyldithiocarbamate (1a) with chlorosulfonyl isocyanate in the presence of AlCl₃ gives 5-(N-methylanilino)-1,2,4-dithiazol-3-one (2), 1-methyl-2-propylthio-4-quinazolinone (3) and N-methyl-N-phenyl-S-propylthiocarbamate (4a) in addition to 3-propylthio-4H-1,2,4-benzothiadiazine 1,1-dioxide (5). However, the same reaction conducted without AlCl₃ gives 2, 4a, and (Z)-N-methyl-N-phenyl-N‘-chlorosulfonylcarbamimidoyl chloride (6). Compound (2) exhibited fungicidal and antibacterial activities.