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Sulfamide

Organosulfur compound

Organosulfur compound

Sulfuryl amide | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S =

Sulfamide (IUPAC name: sulfuric diamide) is a compound with the chemical formula and structure . 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: :[[Image:SulfonamideSynthesisfromSO2.png|400px|Sulfonamide synthesis from aniline and sulfur dioxide]]

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

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

References

References

  1. ''[[Merck Index]]'', 11th Edition, '''8894'''.
  2. fr. Annales de chimie et de physique, series 2, '''69''' : 170-184; see especially "{{lang. fr. Action de gaz ammoniac sec sur la liqueur chlorosulfurique" (Action of dry ammonia gas on liquid sulfuryl chloride), pages 176-180.
  3. (2006). "Sulfamides and sulfamide polymers directly from sulfur dioxide". Chemical Communications.
  4. (2009). "The Role of Sulfamide Derivatives in Medicinal Chemistry: A Patent Review (2006 – 2008)". Expert Opinion on Therapeutic Patents.
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sulfuryl-compounds inorganic-nitrogen-compounds sulfamides
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