Sulfamide

Sulfamide[1]
Names
	IUPAC name Sulfuric diamide
	Other names Sulphamide; Sulfuryl amide
Identifiers
CAS Number	7803-58-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29368 ;
ChEMBL	ChEMBL355001 ;
ChemSpider	74243 ;
ECHA InfoCard	100.029.330
PubChem CID	82267;
UNII	VS7TZW634V ;
CompTox Dashboard (EPA)	DTXSID5064885 ;
	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)	-44.4·10−6 cm3/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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

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]

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]

References

Merck Index, 11th Edition, 8894.
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.
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.
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.

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[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.

[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.

Sulfamide

Sulfamide functional group

See also

References