4- Chloro-1,2,3-dithiazole-5-thione

If benzamidine is replaced by benzamidoxime, then the 4-oxide derivative 107 is obtained as a minor product (8%) together with 4-chloro-l,2,3-dithiazol-5-one 108 (32%) and the 5-thione 109 (15%) (Equation 30). The formation of the 4-oxide, as opposed to the isomeric 2-oxide, was confirmed by mass spectral and 15N NMR data. The yield of the 4-oxide product could be improved by using an O-acyl benzamidoxime in place of benzamidoxime <1999J(P1)2243>. 

The IR spectrum of 4-chloro-l,2,3-dithiazole-5-thione 41 shows strong bands at 1041, 1029, and 1013cm 1 in the region for sulfine symmetric and asymmetric stretching <1998J(P1)2505>. 

Primary and secondary alkylamines have been used for the preparation of iV-alkyl- and V,lV-dialkylcyanothio-formamides, respectively, in the reaction with 4-chloro-l,2,3-dithiazole-5-thione 41 (Equation 20) <1996TL3709>. 4-Chloro-l,2,3-dithiazole-5-one 99 in the reaction with mono- and di-alkylamines afforded N,N -disubstituted ureas in moderate to good yields (Equation 21) <2001TL8197>. The reaction was proposed to be similar to the corresponding thione 41 but displacement of a cyano group by another molecule of alkylamine accompanies this conversion. 

Compound 553, obtained from Apple s salt 552 or from 4-chloro-l,2,3-dithiazole-5-thione, reacts with several nucleophiles affording highly functionalized 5-cyano isothiazoles 554 in a very short and simple synthesis from readily available materials <1997J(P 1)3345, 1998J(P1)77, 2002J(P1)1236>. 

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