[54585-47-6] · C8H8N2S · 1,2-Dihydro-4,6-dimethyl-2-thioxo-3-pyridinecarbonitrile · (MW 164.22)
(for access to the corresponding disulfide for use in synthesis of esters, lactones, and amides from carboxylic acids)
Physical Data: mp 250-264 °C (dec).
Solubility: sparingly sol toluene and CH2Cl2.
Form Supplied in: crystalline solid.
Preparative Method: the reagent (1) is prepared in essentially quantitative yield by reaction of 2-cyanothioacetamide with 2,4-Pentanedione.1 The corresponding disulfide (2) [bis(3-cyano-4,6-dimethylpyridinyl) disulfide] is prepared by oxidation of (1) with Iodine under basic conditions.2
Handling, Storage, and Precautions: the reagent should be treated as a potential irritant.
The principal synthetic application of the reagent (1) is as a source of the corresponding symmetrical disulfide (2) (eq 1).2 The disulfide (2) is used to effect esterifications (eqs 2-4)3,4 and amidations (eqs 5 and 6)5,6 (see also 2,2´-Dipyridyl Disulfide).
University of Bristol, UK