Sulfamide

Short description: Organosulfur compound

Sulfamide[1]

Names
IUPAC name

Sulfuric diamide

Preferred IUPAC name

Sulfamide

Other names

Sulphamide
Sulfuryl amide

Identifiers

CAS Number

* 7803-58-9 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:29368 Y

ChEMBL |

* ChEMBL355001 Y

ChemSpider |

* 74243 Y

PubChem CID

* 82267

UNII |

* VS7TZW634V Y

InChI

* InChI=1S/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4) Y

Key: NVBFHJWHLNUMCV-UHFFFAOYSA-N Y

* 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

| H

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).

N verify (what is YN ?)
Infobox references

Sulfamide (IUPAC name: sulfuric diamide) is a compound with the chemical formula SO
2(NH

2 and structure H
2N–S(=O)
2–NH
2. 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 (Et
3N, Et = ethyl group), and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et
3N–+
–I−
, Et
3N–I+
–I−
3 and Et
3N+
–SO−

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

## See also

* Sulfamic acid
* Sulfonamide

## 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.

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*[CID]: Compound ID