Sulfamide

Sulfamide (IUPAC name: sulfuric diamide) is a compound with the chemical formula SO₂(NH₂)₂ and structure H₂N−S(=O)₂−NH₂. Sulfamide is produced by the reaction of sulfuryl chloride with ammonia. Sulfamide was first prepared in 1838 by the French chemist Henri Victor Regnault.

Sulfamide functional group

In organic chemistry, the term sulfamide may also refer to the functional group which consists of at least one organic group attached to a nitrogen atom of sulfamide.

Symmetric sulfamides can be prepared directly from amines, sulfur dioxide gas and an oxidant:

In this example, the reactants are aniline, triethylamine (Et₃N, Et = ethyl group), and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et₃N−⁺−I⁻, Et₃N−I⁺−I−3 and Et₃N⁺−SO−2.

The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.

See also

• Sulfamic acid
• Sulfonamide

References