Misplaced Pages

Sulfamide

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Organosulfur compound
Sulfamide
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.029.330 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4)Key: NVBFHJWHLNUMCV-UHFFFAOYSA-N
  • InChI=1/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4)Key: NVBFHJWHLNUMCV-UHFFFAOYAV
SMILES
  • 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 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) 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.

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:

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.

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.
Categories: