Sulfamide

Sulfamide[1]
IUPAC name

Sulfuric diamide
Other names

Sulfamide
Sulfuryl amide
Identifiers
CAS number 7803-58-9 Y
PubChem 82267
ChemSpider 74243 Y
ChEBI CHEBI:29368 N
ChEMBL CHEMBL355001 Y
Jmol-3D images Image 1
Properties
Molecular formula H4N2O2S
Molar mass 96.11 g/mol
Appearance White orthorhombic plates
Melting point

93 °C, 366 K, 199 °F
Boiling point

250 °C, 523 K, 482 °F (decomposition)
Solubility in water Freely soluble
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sulfamide (IUPAC name: sulfuric diamide) is a chemical compound with the molecular structure H2NSO2NH2. Sulfamide is produced by the reaction of sulfuryl chloride with ammonia.

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 and sulfur dioxide gas[2]:

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-.

The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.[3]

See also

References

  1. ^ Merck Index, 11th Edition, 8894.
  2. ^ Sulfamides and sulfamide polymers directly from sulfur dioxide Alexander V. Leontiev, H. V. Rasika Dias and Dmitry M. Rudkevich Chem. Commun., 2006, 2887 - 2889, doi:10.1039/b605063h
  3. ^ Allen B Reitz‌, Garry R Smith‌, and Michael H Parker‌ (2009). "The role of sulfamide derivatives in medicinal chemistry: a patent review (2006 – 2008)". Expert Opinion on Therapeutic Patents 19 (10): 1449–1453. doi:10.1517/13543770903185920.