[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).

1. Schmidt, U.; Kubitzek, H. CB 1960, 93, 1559.
2. Schmidt, U.; Giesselmann, G. CB 1960, 93, 1590.
3. Schmidt, U.; Heermann, D. AG(E) 1979, 18, 308.
4. Schmidt, U.; Werner, J. S 1986, 986.
5. Schmidt, U.; Schefenacker, K. LA 1985, 1254.
6. Schmidt, U.; Potzolli, B. LA 1987, 935.

Timothy Gallagher

University of Bristol, UK

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