1-(Methyldithiocarbonyl) imidazole

CAS 74734-11-5, Cat. No EN300-7247412
Reagent for thiocarbonyl transfer

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1-(Methyldithiocarbonyl) imidazole is a yellow crystalline solid, soluble in most common organic solvents, and stable under cool and dry conditions^1,2. The reagent is widely used because it efficiently transfers a thiocarbonyl group. It forms dithiocarbonates (xanthates) from alcohols in excellent yields (>95%), and dithiocarbamates from amines or anilines, with even higher efficiency when its methyl iodide adduct is used. It also produces thioureas and heterocyclic thiones from diamines or amino alcohols, giving both symmetrical and unsymmetrical products in good yields. The key application is in the synthesis of 2-thiohydantoins³: in three-component couplings with amino esters and amines, it provides 3,5- and 1,3,5-substituted or fused thiohydantoins in yields of 87–97%, often with good stereochemical integrity. In summary, it is a practical, safe, and versatile alternative to the traditional CS₂/MeI system for thiocarbonyl transfer, with broad use in the synthesis of sulfur-containing heterocycles and thioureas.

Synonyms: 1H-Imidazole-1-carbodithioic acid, methyl ester; methyl 1H-imidazole-1-carbodithioate