Abstract
[73371-99-0] C6H4ClNOS (MW 173.63) InChI = 1S/C6H4ClNOS/c7-6(9)10-5-3-1-2-4-8-5/h1-4H InChIKey = KAFAIALSGSIJFN-UHFFFAOYSA-N (convenient preparation of 2-pyridylthiol esters;2 subsequent transformation into lactones,3 peptides,4 and ketones5) Physical Data: 1H NMR (CDCl3) δ 8.64 m (1H), 7.75 m (2H), 7.38 m (1H). Solubility: sol CH2Cl2, ether. Form Supplied in: colorless oil; main impurity is bis(thiopyridyl) carbonate; not commercially available. Analysis of Reagent Purity: IR (CH2Cl2) 1765 cm−1 (CO); main impurity: IR (CH2Cl2) 1715 cm−1 (CO). Preparative Method: Phosgene (5 equiv) in toluene and CH2Cl2 is cooled to 0 °C. Dropwise addition (5 min) of a CH2Cl2 solution of Triethylamine (slight excess) and 2-Pyridinethiol is followed by stirring for 10 min. After removal of excess phosgene and CH2Cl2 in vacuo, hexane is added and the resulting precipitate is filtered. After concentration of the combined filtrates, the colorless oil (96%) is dissolved in CH2Cl2 and stored at −25 °C. Handling, Storage, and Precautions: very unstable to water and silica gel; however, it can be handled in air. It is stable for one month if stored at −25 °C. Since phosgene is used in preparing this reagent, preparation should be in a working fume hood and extreme caution is required.
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