Sulfamide

Organosulfur compound
Sulfamide[1]
Ball-and-stick model of the sulfamide molecule
Names
IUPAC name
Sulfuric diamide
Preferred IUPAC name
Sulfamide
Other names
Sulphamide
Sulfuryl amide
Identifiers
CAS Number
  • 7803-58-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:29368 checkY
ChEMBL
  • ChEMBL355001 checkY
ChemSpider
  • 74243 checkY
ECHA InfoCard 100.029.330 Edit this at Wikidata
PubChem CID
  • 82267
UNII
  • VS7TZW634V checkY
CompTox Dashboard (EPA)
  • DTXSID5064885 Edit this at Wikidata
InChI
  • InChI=1S/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4) checkY
    Key: NVBFHJWHLNUMCV-UHFFFAOYSA-N checkY
  • InChI=1/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4)
    Key: NVBFHJWHLNUMCV-UHFFFAOYAV
  • O=S(=O)(N)N
Properties
Chemical 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
Magnetic susceptibility (χ)
 -44.4×10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Sulfamide (IUPAC name: sulfuric diamide) is a compound with the chemical formula SO2(NH2)2 and structure H2N−S(=O)2−NH2. 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

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:[3]

Sulfonamide synthesis from aniline and sulfur dioxide

In this example, the reactants are aniline, triethylamine (Et3N, Et = ethyl group), and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et3N−+−I−, Et3N−I+−I−3 and Et3N+−SO−2.

The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.[4]

See also

References

  1. ^ Merck Index, 11th Edition, 8894.
  2. ^ Regnault, Victor (1838) "Sur l'acide chlorosulfurique et la sulfamide" (On sulfuryl chloride 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. PMID 17007406.
  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. S2CID 6561685.