Abstract
[3005-50-3] C6H6N4OS (MW 182.23) (forms N-acylimidazolides1 used to synthesize amides, peptides,2 esters,3 and ketones;4 synthesis of symmetrical sulfoxides,5 inorganic esters,6 and N-alkylimidazoles7) Alternate Names: N,N′-thionylimidazole; N,N′-thionyldiimidazole; TDI. Physical Data: mp 78–79 °C. Solubility: sol THF, CH2Cl2, toluene. Form Supplied in: not commercially available; usually used in THF solution. Analysis of Reagent Purity: usual preparations are used immediately without analysis. Preparative Method: the reagent is prepared by reacting Thionyl Chloride with 4 equiv of Imidazole in anhydrous THF at 0 °C. The precipitated imidazole hydrochloride is filtered and the solution is pure enough to use.8 Purification: filter to remove imidazole hydrochloride. Analytically pure samples have been prepared by reaction of thionyl chloride and N‐(Trimethylsilyl)imidazole.9 Handling, Storage, and Precautions: extremely hygroscopic; reacts exothermically with water and alcohols. Store as a solution in THF or CH2Cl2 under dry N2.8b Use in a fume hood.
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