Imidoylbenzotriazoles: Stable Alternatives to Imidoyl Chlorides

Imidoylhenzotriazoles were prepared from the corresponding amides and 1.1'-sulfinyldibenzotriazole, generated in situ from l-trimethylsilylbenzotriazole and thionyl chloride.The imidoylbenzotriazoles are stable precursors for the synthesis of imidates and thioimidates.Imidoyl chlorides are useful and versatile intermediates in organic synthesis.'They are precursors for the synthesis of a multitude of functional groups such as imidates,' thioimidates?a m i d i n e ~, ~ imidoyl cyanides,j alkylated imines6 etc. Imidoyl chlorides are generally prepared in situ by treatment of the corresponding amides with phosgene, diphosgene, oxdyl dichloride, phosphorus pentachloride, phosphorus trichloride or arylphosphorane ~hlorides.'~Although the preparation of imidoyl chlorides normally provides good yields, side-reactions such as self-condensation have been reported at elevated temperatures if a-CH groups are