Sulfamide

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Sulfamide[1]
Sulfamide.png
Identifiers
CAS number 7803-58-9 N
PubChem 82267
ChemSpider 74243 YesY
ChEBI CHEBI:29368 YesY
ChEMBL CHEMBL355001 YesY
Jmol-3D images Image 1
Properties
Molecular formula H4N2O2S
Molar mass 96.11 g/mol
Appearance White orthorhombic plates
Melting point 93 °C (199 °F; 366 K)
Boiling point 250 °C (482 °F; 523 K) (decomposes)
Solubility in water Freely soluble
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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 was first prepared in 1838 by the French chemist Henri Victor Regnault.[2]

Sulfamide functional group[edit]

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:[3]

Sulfonamide synthesis from aniline and sulfur dioxide

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.[4]

See also[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 8894.
  2. ^ Regnault, Victor (1838) "Sur l'acide chlorosulfurique et la sulfamide" (On sulfuryl choride and sulfamide), Annales de chimie et de physique, series 2, 69 : 170-184; see especially "Action de gaz ammoniac sec sur la liqueur chlorosulfurique" (Action of dry ammonia gas on liquid sulfuryl chloride), pages 176-180.
  3. ^ Leontiev, A. V.; Dias, H. V. R.; Rudkevich, D. M. (2006). "Sulfamides and sulfamide polymers directly from sulfur dioxide". Chemical Communications 2006 (27): 2887–2889. doi:10.1039/b605063h. 
  4. ^ Reitz‌, A. B.; Smith‌, G. R.; Parker‌, M. H. (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. PMID 19650745.