Sulfonamide (chemistry)

A sulfonamide (compound) is a compound that contains this group. The general formula is RSO₂NH₂, where R is some organic group. For example, "methanesulfonamide" is CH₃SO₂NH₂. Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group with an amine group.

In medicine, the term "sulfonamide" is sometimes used as a synonym for sulfa drug, a derivative or variation of sulfanilamide.

Organic synthesis

• The reaction of sulfonyl chlorides with amines in the synthesis of sulfonylmethylamide . A readily available sulfonyl chloride source is tosyl chloride.
• Symmetric sulfonamides are prepared directly from amines and sulfur dioxide gas:

In this example, the reactants are aniline, triethylamine, and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et₃N-I⁺-I^-, Et₃N-I⁺-I₃^- and Et₃N⁺-SO₂^-.

See also

• Sulfonamide (medicine)
• Sulfamic acid
• Sulfamide

References