Thioamide

Thionamides ( Thiosäureamide ) derived from the amide (more precisely, carboxamides ) in which the carbonyl oxygen atom of the amide has been replaced by a sulfur atom. The thionamides are resonance-stabilized.

Synthesis

The most common method for the synthesis of Thiosäureamiden based on the addition of hydrogen sulfide to nitriles:

According to this method, however, only thionamides are available that contain two bonded hydrogen atoms on the nitrogen atom. For the synthesis of highly substituted thionamides starts from amides and sets them with the Lawesson's reagent or phosphorus pentasulfide to in an inert solvent:

Reactivity

The synthetically important reaction of Thiosäureamide consists in the synthesis of numerous heterocycles such as thiazoles.

Representative

An important representative of this class is the herbicide chlorthiamid.