Sulfamides

Sulfamides are a class of organosulfur compounds that contain the sulfamide functional group, in which a sulfur atom is bonded to two oxygens and to two nitrogens. The simplest member is sulfamide, with the formula H2N–SO2–NH2. In substituted sulfamides, one or both nitrogens bear organic substituents, giving mono-substituted and di-substituted derivatives.

The core feature of sulfamides is the sulfonyl sulfur linked to two nitrogens. The parent sulfamide has two N–H bonds, enabling hydrogen bonding and relatively high polarity. Substituting one or both nitrogens with alkyl or aryl groups changes solubility, basicity, and reactivity, producing a wide range of mono- and di-substituted sulfamides used in synthesis.

Sulfamides are typically prepared by coupling reactions involving sulfamoyl chlorides (for example, ClSO2NH2) with amines under basic conditions. They can also be formed from sulfamic acid derivatives and amines in condensation-type processes. The choice of substituents on the nitrogens influences reactivity in subsequent transformations.

Properties of sulfamides include their polar, hydrogen-bond-donating character and relatively low basicity of the nitrogens compared with simple amines. They are generally stable under normal lab conditions and can participate as building blocks in organic synthesis. In practice, sulfamides serve as versatile scaffolds in medicinal chemistry and related fields, and as precursors or linkages in diverse chemical syntheses.