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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.029.330
UNII
  • 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
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)
Freely soluble
-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).
☒N verify (what is checkY☒N ?)
Infobox references

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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.